HCID 18477041, compound → HCID 57051639, compound

HRID 2188449Notes

Reaction equation

HRID 2188449 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(O)(=O)CC(O)=O.[NH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][NH:54][S:55]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)(=[O:57])=[O:56]>>[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:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][NH:54][S:55]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)(=[O:57])=[O:56])[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 18477041HCID 18477041, 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 57051639HCID 57051639, compoundYield 162.5%

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 (45 mg) and N-(5-aminopentyl)-benzenesulphonamide malonate (45 mg, 0.08 mmol) according to Method C with HPLC purification to give the title compound (4.2 mg, 0.13 mmol). 1H-NMR (400 MHz, CD3OD) δ 0.97 (m, 1H) 1.16-1.49 (m, 16H) 2.73-3.16 (m, 6H) 4.26 (m, 1H) 4.50 (m, 1H) 4.68 (s, 2H) 7.09-7.9 (m, 13H); HRMS 754.2859 (calc of monoisotopic mass for C37H46N4O11S gives 754.2884).

Workup

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

Sources & evidence

ORD record
ord-8e9ede351ef3417794edaec73c398353
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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