HCID 13414463, compound → HCID 22084009, compound

HRID 2188460Notes

Reaction equation

HRID 2188460 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].Cl.Cl.[CH2:43]([NH:50][CH:51]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH2:52][NH2:53])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[CH2:43]([NH:50][CH:51]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH2:52][NH:53][C:14](=[O:15])[C@@H:13]([NH:12][C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[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:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

3

Reactant 2

HCID 13414463HCID 13414463, 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 22084009HCID 22084009, compoundYield 11.5%

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 (70 mg, 0.13 mmol) and N1-benzyl-1-phenyl-1,2-ethandiamine dihydrochloride (45 mg, 0.15 mmol) according to Method C with HPLC purification to give the title compound (11 mg) as a diastereomeric mixture. 1H-NMR (400 MHz, CD3OD) d 7.50 (1H), 7.45-7.03 (17H), 4.40 (m, 1H), 4.25 (m, 1H), 4.06 (m, 1H), 3.80 (s, 2H), 3.03 (m, 1H), 1.33 (s, 9H); HRMS m/z 738.3281 (calc. of monoisotopic mass for C41H46N4O9 gives 738.3265).

Workup

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

Sources & evidence

ORD record
ord-9d5316fa28f446c8ad7ea59d33e08cdc
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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