1-(2-Aminoethyl)pyrrolidin-2-one → HCID 70161037, compound

HRID 2188447Notes

Reaction equation

HRID 2188447 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].[NH2:41][CH2:42][CH2:43][N:44]1[CH2:48][CH2:47][CH2:46][C:45]1=O>>[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](=[O:15])[NH:41][CH2:42][CH2:43][N:44]1[CH2:48][CH2:47][CH2:46][CH2:45]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])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 906601-(2-Aminoethyl)pyrrolidin-2-oneHCID 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 70161037HCID 70161037, compoundYield 8.9%

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 N-(2-aminoethyl)-pyrrolidinone (33 mg, 0.29 mmol) according to Method C with HPLC purification to give the title compound (10 mg). 1H-NMR (400 MHz, CD3OD) δ 1.36 (s, 9H) 2.05 (s, 4H) 2.68-3.20 (m, 8H) 3.39 (m, 4H) 4.28 (m, 1H) 4.39 (m, 1H) 4.69 (s, 2H) 7.05-7.40 (m, 7H) 7.52 (s, 1H); HRMS m/z 626.2929 (calc. of monoisotopic mass for C32H42N4O9 gives 626.2952).

Workup

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

Sources & evidence

ORD record
ord-81a56d00ed574c6fb5fa5d94ba404fd4
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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