HCID 18477000, compound → HCID 57227752, compound

HRID 2188443Notes

Reaction equation

HRID 2188443 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][CH:43]([CH3:62])[CH2:44][C:45]1[C:53]2[C:48](=[CH:49][CH:50]=[C:51]([O:54][CH2:55][C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[CH:52]=2)[NH:47][CH:46]=1>>[CH2:55]([O:54][C:51]1[CH:52]=[C:53]2[C:48](=[CH:49][CH:50]=1)[NH:47][CH:46]=[C:45]2[CH2:44][CH: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]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])[CH3:62])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

Participants

3

Reactant 2

HCID 18477000HCID 18477000, 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 57227752HCID 57227752, compoundYield 33.6%

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 (68 mg, 0.12 mmol) and 3-(2-aminopropyl)-5-(benzyloxy)-indole hydrochloride (46 mg, 0.15 mmol) according to Method C with HPLC purification to give the title compound (32 mg) as a diasteromeric mixture. IR (KBr) 3409, 1681, 1652 cm−1; HRMS m/z 792.3360 (calc. of monoisotopic mass for C44H48N4O10 gives 792.3370).

Workup

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

Sources & evidence

ORD record
ord-006249ce1ed34b36b48d99c9e51cc18a
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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