HCID 18477049, compound → HCID 57273314, compound

HRID 2188455Notes

Reaction equation

HRID 2188455 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][CH:43]([C:45]1[CH:50]=[C:49]([Cl:51])[CH:48]=[CH:47][C:46]=1[O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[OH:44]>>[CH2:53]([O:52][C:46]1[CH:47]=[CH:48][C:49]([Cl:51])=[CH:50][C:45]=1[CH:43]([OH:44])[CH2:42][NH:41][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])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

3

Reactant 2

HCID 18477049HCID 18477049, compoundHCID 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 57273314HCID 57273314, compoundYield 64.2%

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 (75 mg, 0.13 mmol) and 2-amino-1-[2-(benzyloxy)-5-chlorophenyl]-1-ethanol (45 mg, 0.16 mmol) according to Method C to give the title compound (66 mg) as a diasteromeric mixture. 1H-NMR (400 MHz, CD3OD) d 4.77 (s, 1H), 4.75 (s, 1H), 4.55 (m, 1H), 4.22 (m, 1H), 1.33-1.32 (9H); HRMS m/z 789.2713 (calc. of monoisotopic mass for C41H44ClN3O11 gives 789.2664).

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-71dba95babfb4046bc9b65510fa0b75c
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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