2-(Benzylsulfanyl)ethan-1-amine--hydrogen chloride (1/1) → HCID 70161047, compound

HRID 2188458Notes

Reaction equation

HRID 2188458 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](OCC(OC)=O)=[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].Cl.[CH2:42]([S:49][CH2:50][CH2:51][NH2:52])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH2:42]([S:49][CH2:50][CH2:51][NH:52][C:14](=[O:15])[C@@H:13]([NH:12][C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:6]([O:5][CH3:1])=[O:7])=[C:20]([CH:19]=1)[C:30]([OH:32])=[O:31])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

3

Reactant 2

HCID 131661882-(Benzylsulfanyl)ethan-1-amine--hydrogen chloride (1/1)HCID 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 70161047HCID 70161047, compoundYield 25.1%

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 2-(benzylsulfanyl)-1-ethanamine hydrochloride (44 mg, 0.22 mmol) according to Method C with HPLC purification to give the title compound (15 mg). 1H-NMR (400 MHz, CD3OD) d 7.76 (s, 1H), 6.97 (d, J=8.6 Hz, 1H), 4.77 (s, 2H), 4.51 (m, 1H), 4.24 (dd, J=5.1 Hz, J=9.3 Hz, 1H), 3.71 (s, 2H), 3.19 (m, 1H), 2.74 (m, 1H), 2.41 (m, 2H), 1.35 (s, 9H); HRMS m/z 679.2542 (calc. of monoisotopic mass for C34H41N3O9S gives 679.2564).

Workup

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

Sources & evidence

ORD record
ord-51a8e24219744274affc132b55f7ac78
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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