Homoallyl bromide → (2R,3S) N1-[(3S)-1,3-dihydro-1-methyl-2-oxo-5-phenyl-2H-1,4-benzodiazepin-3-yl]-2-(2-methylpropyl)-3-(3-buten-1-yl)-butanediamide

HRID 272524

반응식

HRID 272524 반응식
[CH2:1](Br)[CH2:2][CH:3]=C.[CH3:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:10][CH:9]([NH:24][C:25](=[O:47])[C@H:26]([CH2:43][CH:44]([CH3:46])[CH3:45])[C@H:27]([CH2:40]C=C)[C:28]([NH:30]CC2C=C(F)C=C(F)C=2)=[O:29])[C:8]1=[O:48].C([O-])(=O)CCC([O-])=O.CN1C2C=CC=CC=2C(C2C=CC=CC=2)=NC(N)C1=O>>[CH3:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:10][C@H:9]([NH:24][C:25](=[O:47])[C@H:26]([CH2:43][CH:44]([CH3:45])[CH3:46])[C@H:27]([CH2:40][CH2:3][CH:2]=[CH2:1])[C:28]([NH2:30])=[O:29])[C:8]1=[O:48]

참가 물질

5

반응물 4

HCID 21241Homoallyl bromideHCID 160419SuccinateHCID 27296813-Amino-1-methyl-5-phenyl-1H-benzo[E][1,4]diazepin-2(3H)-oneHCID 9916426(2R,3S)N1-[1,3-dihydro-1-methyl-2-oxo-5-phenyl-2H-1,4-benzodiazepin-3-yl]-2-(2-methylpropyl)-3-allyl-N4-[3,5-difluorobenzyl]-butanediamide

생성물 1

HCID 9912782(2R,3S) N1-[(3S)-1,3-dihydro-1-methyl-2-oxo-5-phenyl-2H-1,4-benzodiazepin-3-yl]-2-(2-methylpropyl)-3-(3-buten-1-yl)-butanediamide

실험 절차

A procedure analogous to the preparation of Example 5 was followed. The appropriate succinate ester was prepared using the method disclosed in PCT publication WO 98/51665), using 3-butenyl bromide for R3—X in place allyl bromide (see Scheme 2). The anti-succinate half-ester was coupled to (S)-isomer benzodiazepine (30) using the procedures of Step 1. After Steps 2 and 3, the title compound was isolated. MS (M+H)+=475.3; (M+Na)+=497.3.

후처리

  1. customA procedure analogous to the preparation of Example 5

출처 및 근거

ORD 기록
ord-3fc39e7433a24db287670b7b6d2de22a
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456172B2

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