Benzenemethanamine, 3,4-dichloro- → HCID 57978312, compound

HRID 1866553Notes

Reaction equation

HRID 1866553 reaction equation
[Si:1]([O:8][C@H:9]([C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([CH2:34][OH:35])[CH:28]=1)[CH2:10][NH:11][C:12]([CH3:26])([CH3:25])[CH2:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][C:22](O)=[O:23])[CH:17]=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[Cl:45])[CH2:40][NH2:41]>>[Si:1]([O:8][C@H:9]([C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([CH2:34][OH:35])[CH:28]=1)[CH2:10][NH:11][C:12]([CH3:25])([CH3:26])[CH2:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][C:22]([NH:41][CH2:40][C:39]2[CH:42]=[CH:43][C:44]([Cl:45])=[C:37]([Cl:36])[CH:38]=2)=[O:23])[CH:17]=[CH:18][CH:19]=1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 69025804HCID 69025804, compound

Product 1

HCID 57978312HCID 57978312, compoundYield 64%

Procedure

The title compound was prepared from 3-{3-[2-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl )phenyl]ethyl}amino)-2-methylpropyl]phenyl}propanoic acid (preparation 144) and 3,4-dichlorobenzylamine, using a method similar to that of preparation 38, as a clear oil in 64% yield. 1H NMR (400 MHz, CD3OD) δ: 7.40 (3H, m), 7.18 (1H, m), 7.08 (5H, m), 6.78 (1H, d), 4.61 (3H, m), 4.23 (2H, s), 2.90 (3H, m), 2.60 (5H, m), 1.08 (3H, s), 1.04 (3H, s), 0.81 (9H, s), 0.00 (3H, s), -0.18 (3H, s) ppm; LRMS ESI m/z 659 [M+H]+

Workup

  1. customof preparation 38

Sources & evidence

ORD record
ord-a390037918fa41c2b9830bce82a89678
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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