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【结 构 式】 
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【分子编号】45997 【品名】2'-(aminomethyl)[1,1'-biphenyl]-3-carboxylic acid 【CA登记号】 |
【 分 子 式 】C14H13NO2 【 分 子 量 】227.26276 【元素组成】C 73.99% H 5.77% N 6.16% O 14.08% |
合成路线1
该中间体在本合成路线中的序号：(VII)3-Iodobenzoic acid (I) was converted to ethyl ester (II) by treatment with DCC and DMAP in ethanol. Subsequent Suzuki coupling of (II) with 2-formylbenzeneboronic acid (III) furnished the biphenyl derivative (IV). Formation of oxime (V) using hydroxylamine hydrochloride, followed by reduction with zinc metal and HOAc, afforded amino ester (VI). Saponification of the ethyl ester (VI) gave amino acid (VII), which was coupled with Fmoc-L-valine (VIII) by means of HBTU to yield amide (IX). This compound was attached to Wang resin using DIPC and DMAP to produce resin (X). Deprotection of the Fmoc group by means of piperidine in DMF then gave the corresponding amino compound (XI). To this were incorporated protected amino acid Fmoc-L-lysine(Z) (XII) followed by a deprotection step with piperidine in DMF, to yield the resin-bound peptide (XIII). (Scheme 29421701a)
| 【1】 DeGrado, W.F.; Singh, G.; Reisine, T.; Suich, D.J.; Liapakis, G.; Mousa, S.A.; Template-constrained cyclic peptide analogues of somatostatin: Subtype-selective binding to somatostatin receptors and antiangiogenic activity. Bioorg Med Chem 2000, 8, 9, 2229. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX),(X) | 45998 | 2'-[[((2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-methylbutanoyl)amino]methyl][1,1'-biphenyl]-3-carboxylic acid | C34H32N2O5 | 详情 | 详情 | |
| (I) | 45991 | 3-iodobenzoic acid | 618-51-9 | C7H5IO2 | 详情 | 详情 |
| (II) | 45992 | ethyl 3-iodobenzoate | 58313-23-8 | C9H9IO2 | 详情 | 详情 |
| (III) | 45993 | 2-formylphenylboronic acid | 40138-16-7 | C7H7BO3 | 详情 | 详情 |
| (IV) | 45994 | ethyl 2'-formyl[1,1'-biphenyl]-3-carboxylate | C16H14O3 | 详情 | 详情 | |
| (V) | 45995 | ethyl 2'-[(hydroxyimino)methyl][1,1'-biphenyl]-3-carboxylate | C16H15NO3 | 详情 | 详情 | |
| (VI) | 45996 | ethyl 2'-(aminomethyl)[1,1'-biphenyl]-3-carboxylate | C16H17NO2 | 详情 | 详情 | |
| (VII) | 45997 | 2'-(aminomethyl)[1,1'-biphenyl]-3-carboxylic acid | C14H13NO2 | 详情 | 详情 | |
| (VIII) | 19932 | (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-methylbutyric acid | C20H21NO4 | 详情 | 详情 | |
| (XI) | 45999 | 2'-([[(2S)-2-amino-3-methylbutanoyl]amino]methyl)[1,1'-biphenyl]-3-carboxylic acid | C19H22N2O3 | 详情 | 详情 | |
| (XII) | 46001 | N-alpha-Fmoc--N-epsilon-Z-L-lysine; Fmoc-Nepsilon-Z-L-lysine; N-epsilon-Z-N-alpha-Fmoc-L-lysine; (2S)-6-[[(benzyloxy)carbonyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]hexanoic acid | 86060-82-4 | C29H30N2O6 | 详情 | 详情 |
| (XIII) | 46000 | 2'-[(4S,7S)-7-amino-4-isopropyl-3,6,13-trioxo-15-phenyl-14-oxa-2,5,12-triazapentadec-1-yl][1,1'-biphenyl]-3-carboxylic acid | C33H40N4O6 | 详情 | 详情 |