HCID 22989894, compound → HCID 86758285, compound

HRID 2188459Notes

Reaction equation

HRID 2188459 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.[NH2:42][O:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[CH:47][CH:46]=1>>[C:48]1([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:49]=[CH:50][C:45]([CH2:44][O:43][NH:42][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]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([OH:28])=[O:27])=[C:20]([CH:19]=2)[C:30]([OH:32])=[O:31])=[CH:46][CH:47]=1

Participants

3

Reactant 2

HCID 22989894HCID 22989894, 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 86758285HCID 86758285, compoundYield 41.3%

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 (91 mg, 0.16 mmol) and 4-[(aminooxy)methyl]-1,1′-biphenyl hydrochloride (46 mg, 0.20 mmol) according to Method C with HPLC purification to give the title compound (47 mg). 1H-NMR (400 MHz, CD3OD-Me2SO-d6) d 7.74-7.16 (17H), 4.84 (1H), 4.76 (1H), 4.64 (s, 2H), 4.32 (m, 1H), 3.03 (m, 3H), 1.41 (s, 9H); IR (KBr) 3272, 2978, 1681, 1652 cm−1; HRMS m/z 711.2831 (calc. of monoisotopic mass for C39H41N3O10 gives 711.2792).

Workup

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

Sources & evidence

ORD record
ord-671021a71a194f49ade1c8ead87dbd77
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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