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【结 构 式】

【分子编号】47323

【品名】2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-3-yl)acetic acid

【CA登记号】

【 分 子 式 】C15H19N3O3

【 分 子 量 】289.33428

【元素组成】C 62.27% H 6.62% N 14.52% O 16.59%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

Solid phase synthesis: Attachment of 8-Fmoc-3-carboxymethyl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (I) to Wang resin by means of 2,6-dichlorobenzoyl chloride (A) in DMF in the presence of pyridine, followed by treatment with benzoyl chloride (B) in dichloromethane in the presence of pyridine, provides resin-anchored derivative (II). Treatment of resin (II) with piperidine in DMF allows Fmoc removal to yield deprotected piperidine derivative (III), which is then converted into the target compound by alkylation with 1-(bromomethyl)naphthalene (IV) by heating in DMSO in the presence of DIEA, followed by cleavage of the molecule from the resin by heating with NaOMe in THF/MeOH. Alternatively, the conversion of (III) into the desired compound can be achieved by reductive amination between resin (III) and aldehyde (V) by means of NaBH3CN in THF in the presence of HOAc to afford anchored derivative (VI), followed by cleavage from the resin by heating with NaOMe in THF/MeOH.

1 Watson, B.; Thomsen, C.; Hohlweg, R. (Novo Nordisk A/S); Novel 1,3,8-triazaspiro[4.5]decanones with high affinity for opioid receptor subtypes. EP 1080091; WO 9959997 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 10463 Benzoyl chloride 98-88-4 C7H5ClO 详情 详情
(A) 25087 2,6-dichlorobenzoyl chloride 4659-45-4 C7H3Cl3O 详情 详情
(I),(II) 47322 2-[8-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-3-yl]acetic acid C30H29N3O5 详情 详情
(III) 47323 2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-3-yl)acetic acid C15H19N3O3 详情 详情
(IV) 47324 1-(bromomethyl)naphthalene 3163-27-7 C11H9Br 详情 详情
(V) 12314 1-Naphthaldehyde 66-77-3 C11H8O 详情 详情
(VI) 47325 2-[8-(1-naphthylmethyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-3-yl]acetic acid C26H27N3O3 详情 详情
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