N-(2-Hydrazino-2-oxoethyl)benzamide → HCID 70160972, compound

HRID 2188442Notes

Reaction equation

HRID 2188442 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]([NH:53][NH2:54])(=[O:52])[CH2:42][NH:43][C:44]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:45]>>[C:44]([NH:43][CH2:42][C:41]([NH:53][NH:54][C:14](=[O:15])[C@@H:13]([NH:12][C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=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:52])(=[O:45])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

3

Reactant 2

HCID 349284N-(2-Hydrazino-2-oxoethyl)benzamideHCID 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 70160972HCID 70160972, compoundYield 18.9%

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 hippuric acid hydrazide (42 mg, 0.22 mmol) according to Method C with HPLC purification to give the title compound (24 mg). IR (KBr) 3274, 1652, 1616 cm−1; HRMS m/z 705.2640 (calc. of monoisotopic mass for C35H39N5O11 gives 705.2646).

Workup

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

Sources & evidence

ORD record
ord-97f305d6c6454c47b4eef52dca75ab71
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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