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【结 构 式】 
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【分子编号】63016 【品名】2,2,2-trifluoro-N-[(1S)-2-methyl-1-({(2R)-2-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]pyrrolidinyl}carbonyl)propyl]acetamide; 2,2,2-trifluoro-N-[(1S)-2-methyl-1-({(2R)-2-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]pyrrolidinyl}carbonyl)propyl]acetamide 【CA登记号】 |
【 分 子 式 】C21H32BF3N2O4 【 分 子 量 】444.3023696 【元素组成】C 56.77% H 7.26% B 2.43% F 12.83% N 6.31% O 14.4% |
合成路线1
该中间体在本合成路线中的序号：(IV)In a related synthetic procedure, N-trifluoroacetyl-L-valine (I) is activated as the corresponding acid chloride (II) by treatment with the Vilsmeier reagent in cold EtOAc. Coupling of (II) with the pyrrolidineboronic ester (III) yields amide (IV). The trifluoroacetyl protecting group is then removed by alkaline hydrolysis to produce (V). Finally, deprotection of the boronic acid moiety of (V) with concomitant recycling of the (+)-pinanediol chiral auxiliary is achieved by transesterification with N-Boc-2-pyrrolidineboronic acid (VI) in the presence of methanesulfonic acid to furnish the pinanediol boronate (VII) along with the title compound
| 【1】 Gibson, F.S.; Singh, A.K.; Soumeillant, M.C.; Manchand, P.S.; Humora, M.; Kronenthal, D.R.; A practical synthesis of L-valyl-pyrrolidine-(2R)-boronic acid: Efficient recycling of the costly chiral auxiliary (+)-pinanediol. Org Process Res Dev 2002, 6, 6, 814. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 63014 | (2S)-3-methyl-2-[(2,2,2-trifluoroacetyl)amino]butanoic acid; (2S)-3-methyl-2-[(2,2,2-trifluoroacetyl)amino]butanoic acid | C7H10F3NO3 | 详情 | 详情 | |
| (II) | 63015 | (2S)-3-methyl-2-[(2,2,2-trifluoroacetyl)amino]butanoyl chloride; (2S)-3-methyl-2-[(2,2,2-trifluoroacetyl)amino]butanoyl chloride | C7H9ClF3NO2 | 详情 | 详情 | |
| (III) | 63007 | (2R)-2-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]pyrrolidine | 205116-75-2 | C14H24BNO2 | 详情 | 详情 |
| (IV) | 63016 | 2,2,2-trifluoro-N-[(1S)-2-methyl-1-({(2R)-2-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]pyrrolidinyl}carbonyl)propyl]acetamide; 2,2,2-trifluoro-N-[(1S)-2-methyl-1-({(2R)-2-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]pyrrolidinyl}carbonyl)propyl]acetamide | C21H32BF3N2O4 | 详情 | 详情 | |
| (V) | 63012 | (2S)-2-amino-3-methyl-1-{(2R)-2-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]pyrrolidinyl}-1-butanone | C19H33BN2O3 | 详情 | 详情 | |
| (VI) | 63002 | 1-{[(1,1-dimethylethyl)oxy]carbonyl}-2-pyrrolidinylboronic acid; 1-(tert-butoxycarbonyl)-2-pyrrolidinylboronic acid | 149682-75-7 | C9H18BNO4 | 详情 | 详情 |
| (VII) | 63006 | tert-butyl (2R)-2-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]-1-pyrrolidinecarboxylate | C19H32BNO4 | 详情 | 详情 |