HCID 10700194, compound → HCID 54346932, compound

HRID 366152Notes

Reaction equation

HRID 366152 reaction equation
C(O[C:6](=O)[N:7]([C@@H:9]([C:21](=[O:54])[N:22]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][C:33](=[O:53])[CH2:34][NH:35][C:36]([O:38][CH2:39][CH:40]1[C:52]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[C:46]2[C:41]1=[CH:42][CH:43]=[CH:44][CH:45]=2)=[O:37])[CH3:23])[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)C)(C)(C)C>Cl.C(OCC)(=O)C>[CH:42]1[C:41]2[CH:40]([CH2:39][O:38][C:36](=[O:37])[NH:35][CH2:34][C:33](=[O:53])[NH:32][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[CH2:25][CH2:24][N:22]([CH3:23])[C:21](=[O:54])[C@H:9]([NH:7][CH3:6])[CH2:10][C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]=3)[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]=2[CH:45]=[CH:44][CH:43]=1

Participants

4

Reactant 1

HCID 10700194HCID 10700194, compound

Product 1

HCID 54346932HCID 54346932, compoundYield 117.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-{(1R)-1-[N-(2-{2-[2-((Fluoren-9-ylmethoxycarbonyl)amino)acetylamino]phenyl}ethyl)-N-methylcarbamoyl]-2-(2-naphthyl)ethyl}-N-methylcarbamic acid tert-butyl ester (1.18 g, 1.59 mmol) was dissolved in 3.0 M hydrogen chloride in ethyl acetate (8 ml). The reaction mixture was stirred for 2.25 h at room temperature. The solvent was removed in vacuo. The residue was washed with diethyl ether (3×20 ml) and dried in vacuo to give 1.198 g of crude [(2-{2-[N-methyl-N-((2R)-2-methylamino-3-(2-naphthyl)propionyl)amino]ethyl}phenylcarbamoyl)methyl]carbamic acid (fluoren-9-yl)methyl ester as hydrochloride, which was used for the next step without purification.

Workup

  1. customThe solvent was removed in vacuo
  2. washThe residue was washed with diethyl ether (3×20 ml)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-00569504ef6d400a9cc4cac09bfaa565
Source dataset
uspto-grants-2000_10
Patent number
US06127354

Reaction notes

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