(S)-2-Methoxy-1-phenylethanamine → tert-butyl (3r)-3-({[(1S)-2,2-dimethyl-1-({[(1S)-2-methoxy-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3'-methoxy-2-methylbiphen-4-yl)hexanoate

HRID 1700998Notes

Reaction equation

HRID 1700998 reaction equation
[CH3:1][C:2]([CH3:38])([CH3:37])[C@H:3]([NH:7][C:8]([C@H:10]([CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=2)=[CH:24][CH:23]=1)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:9])[C:4]([OH:6])=O.[CH3:39][O:40][CH2:41][C@@H:42]([NH2:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH3:1][C:2]([CH3:38])([CH3:37])[C@H:3]([NH:7][C:8]([C@H:10]([CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=2)=[CH:24][CH:23]=1)[CH2:11][C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])=[O:9])[C:4]([NH:49][C@@H:42]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:41][O:40][CH3:39])=[O:6]

Participants

3

Reactant 2

HCID 11768756(S)-2-Methoxy-1-phenylethanamineHCID 59875740tert-butyl (3r)-3-({[(1S)-2,2-dimethyl-1-(carboxy)propyl]amino}carbonyl)-6-(3'-methoxy-2-methylbiphen-4-yl)hexanoate

Product 1

HCID 59106438tert-butyl (3r)-3-({[(1S)-2,2-dimethyl-1-({[(1S)-2-methoxy-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3'-methoxy-2-methylbiphen-4-yl)hexanoateYield 81%

Procedure

According to the procedure of Preparation 19 d), tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-(carboxy)propyl]amino}carbonyl)-6-(3′-methoxy-2-methylbiphen-4-yl)hexanoate (660 mg, 1.26 mmol) was reacted with (1S)-2-methoxy-1-phenylethylamine (190 mg, 1.260 mmol). Work-up as above, followed by flash chromatography (eluting with hexane:ethyl acetate=3:1) to give tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-({[(1s)-2-methoxy-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3′-methoxy-2-methylbiphen-4-yl)hexanoate (672 mg, 81%) as a colourless foam.

Workup

  1. washfollowed by flash chromatography (eluting with hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a81533a413ac4a3c9a02f330f3db9f05
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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