2-Ethylhexyl 3-{[2-amino-5-(benzyloxy)phenyl]sulfanyl}propanoate → 2-ethylhexyl 3-{[2-{[(4-{[(2S)-2-(acetylamino)propyl]oxy}phenyl)carbonyl]amino}-5-(benzyloxy)phenyl]sulfanyl}propanoate

HRID 1026270Notes

Reaction equation

HRID 1026270 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[S:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH:23]([CH2:28][CH3:29])[CH2:24][CH2:25][CH2:26][CH3:27])=[O:20].[C:30]([NH:33][C@@H:34]([CH3:46])[CH2:35][O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](O)=[O:42])=[CH:39][CH:38]=1)(=[O:32])[CH3:31]>>[C:30]([NH:33][C@@H:34]([CH3:46])[CH2:35][O:36][C:37]1[CH:38]=[CH:39][C:40]([C:41]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][C:3]=2[S:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH:23]([CH2:28][CH3:29])[CH2:24][CH2:25][CH2:26][CH3:27])=[O:20])=[O:42])=[CH:44][CH:45]=1)(=[O:32])[CH3:31]

Participants

3

Reactant 2

HCID 580474822-Ethylhexyl 3-{[2-amino-5-(benzyloxy)phenyl]sulfanyl}propanoateHCID 677786634-{[(2S)-2-(acetylamino)propyl]oxy}benzoic acid

Product 1

HCID 677784372-ethylhexyl 3-{[2-{[(4-{[(2S)-2-(acetylamino)propyl]oxy}phenyl)carbonyl]amino}-5-(benzyloxy)phenyl]sulfanyl}propanoateYield 66.8%

Procedure

Using 2-ethylhexyl 3-{[2-amino-5-(benzyloxy)phenyl]sulfanyl}propanoate (1.00 g) and 4-{[(2S)-2-(acetylamino)propyl]oxy}benzoic acid (628 mg), and in the same manner as in Example 2, step C, the title compound (1.02 g) was obtained.

Sources & evidence

ORD record
ord-78e4939f7c5847b89028e65c6ced8169
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

Loading…