1-(3-Aminopropyl)-2-pyrrolidinone → 5-((2R)-2-({(2S)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-oxo-3-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}propyl)-2-(carboxymethoxy)benzoic Acid

HRID 2188432Notes

Reaction equation

HRID 2188432 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]([OH:16])=O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:41][CH2:42][CH2:43][CH2:44][N:45]1[CH2:49][CH2:48][CH2:47][C:46]1=[O:50]>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:10]([NH:12][C@@H:13]([C:14](=[O:16])[NH:41][CH2:42][CH2:43][CH2:44][N:45]1[CH2:49][CH2:48][CH2:47][C:46]1=[O:50])[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])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 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 571443825-((2R)-2-({(2S)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-oxo-3-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}propyl)-2-(carboxymethoxy)benzoic AcidYield 22.1%

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 N-(3′-aminopropyl)-2-pyrrolidinone (42 mg, 0.29 mmol) according to Method C with HPLC purification to give the title compound (26 mg). 1H-NMR (400 MHz, CD3OD) δ 1.35 (s, 9H) 1.6 (m, 2H) 2.03 (m, 2H) 2.37 (t, 2H) 2.76 (m, 1H) 2.92-3.10 (m, 5H) 3.14 (t, 2H) 3.42 (t, 2H) 4.25 (m, 1H) 4.5 (m, 1H) 4.78 (s, 2H) 7.05 (d, 1H) 7.23 (dd, 5H) 7.42 (d, 1H) 7.72 (s, 1H); HR-MS m/z 654.2880 (calc. Of monoisotopic mass for C33H42N4O10 gives 654.2901).

Workup

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

Sources & evidence

ORD record
ord-84bf4058f88945978097521b3dbb3ee9
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

Loading…