3-Hydroxy-3-phenylpropanehydrazide → 5-{(2S)-2-({(2S)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[2-(3-hydroxy-3-phenylpropanoyl)hydrazino]-3-oxopropyl}-2-(carboxymethoxy)benzoic Acid

HRID 2188440Notes

Reaction equation

HRID 2188440 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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](O)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:41]1([CH:47]([OH:53])[CH2:48][C:49]([NH:51][NH2:52])=[O:50])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:10]([NH:12][C@H:13]([C:14]([NH:52][NH:51][C:49](=[O:50])[CH2:48][CH:47]([OH:53])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)=[O:15])[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 131524493-Hydroxy-3-phenylpropanehydrazideHCID 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 571753435-{(2S)-2-({(2S)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[2-(3-hydroxy-3-phenylpropanoyl)hydrazino]-3-oxopropyl}-2-(carboxymethoxy)benzoic AcidYield 46.5%

Procedure

Synthesis was performed from (2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[3-(methoxycarbonyl)-4-(2-methoxy-2-oxoethoxy)phenyl]propanoic acid (100 mg, 0.18 mmol) and 3-phenylhydracrylic acid hydrazide (39 mg, 0.22 mmol) according to Method C with HPLC purification to give the title compound (58 mg) as a diasteromeric mixture. 1H-NMR (400 MHz, CD3OD) d 7.77 (1H), 5.11 (dd, J=4.6 Hz, J=8.6 Hz, 1H), 4.78 (2H), 4.70 (m, 1H), 4.24 (dd, J=5.0 Hz, J=9.3 Hz, 1H), 1.34 (s, 9H); IR (KBr) 3274, 1681, 1652, 1608 cm−1; HRMS m/z 692.2670 (calc. of monoisotopic mass for C35H40N4O11 gives 692.2694).

Workup

  1. customSynthesis
  2. customaccording to Method C with HPLC purification

Sources & evidence

ORD record
ord-3b72f3d371194fda8613e6e254ca5fc4
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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