4-Ethoxyaniline → 5-[(2S)-2-({(2S)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-oxo-3-(phenethylamino)propyl]-2-(carboxymethoxy)benzoic Acid

HRID 2188431Notes

Reaction equation

HRID 2188431 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:34]C1C=CC=CC=1)[C:10]([NH:12][C@@H:13]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([O:28]C)=[O:27])=[C:20]([C:30]([O:32]C)=[O:31])[CH:19]=1)[C:14]([OH:16])=O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:41]1(N)[CH:46]=[CH:45][C:44](OCC)=[CH:43][CH:42]=1>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:34][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:10]([NH:12][C@H:13]([C:14](=[O:16])[NH:12][CH2:13][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([OH:28])=[O:27])=[C:20]([CH:19]=1)[C:30]([OH:32])=[O:31])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 90764-EthoxyanilineHCID 57019224(2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[3-(methoxycarbonyl)-4-(2-methoxy-2-oxoethoxy)phenyl]propanoic acid

Product 1

HCID 701610105-[(2S)-2-({(2S)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-oxo-3-(phenethylamino)propyl]-2-(carboxymethoxy)benzoic Acid

Procedure

Synthesis was performed performed from (2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[3-(methoxycarbonyl)-4-(2-methoxy-2-oxoethoxy)phenyl]propanoic acid and phenetylamine (38 uL) according to Method A to give the title compound (57 mg). 1H-NMR (400 MHz, CD3OD) d 7.76 (s, 1H), 7.36 (dd, J=1.9 Hz, J=8.3 Hz, 1H), 7.28-7.15 (m, 10H), 7.00 (d, J=8.7 Hz, 1H), 4.79 (s, 2H), 4.50 (t, J=6.8 Hz, 1H), ), 4.25 (dd, J=5.1 Hz, J=9.4 Hz, 1H), 3.40 (m, 1H), 3.02 (m 2H), 2.90 (dd, J=7.7 Hz, J=13.6 Hz, 1H), 1.36 (s, 9H); (KBr) 3297, 2979, 1728, 1688, 1645 cm−1; HRMS m/z 633.2660 (calc. of monoisotopic mass for C34H39N3O9 gives 633.2686).

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-e5583423e4bb4976871de7978717cb87
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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