Hydrochloric Acid → HCID 68605811, compound

HRID 2267613Notes

Reaction equation

HRID 2267613 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:35]([O:37][CH3:38])=[O:36])[CH:13]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)[S:14][CH2:15][CH2:16][NH:17]C(OC(C)(C)C)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:39]>C(OCC)(=O)C>[ClH:39].[NH2:17][CH2:16][CH2:15][S:14][CH:13]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)[C@@H:12]([C:35]([O:37][CH3:38])=[O:36])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68607668HCID 68607668, compound

Product 1

HCID 68605811HCID 68605811, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of methyl N-[(benzyloxy)carbonyl]-S-{2-[(tert-butoxycarbonyl)amino]ethyl}-3-(1-naphthyl)cysteinate (25b) (3.3 g, 6.13 mmol) in ethyl acetate (80 mL) at −30° C., was bubbled over HCl gas for 10 min, stirred at −30° for 15 min and then allowed to RT for 3 h. Evaporation to near dryness and precipitation from ether afforded pure title compound (25) (2.6 g, 89%) as a white solid. MS APCI, m/z=439 (M+1), 2.34 min.

Workup

  1. waitallowed to RT for 3 h
  2. customEvaporation
  3. customdryness and precipitation from ether afforded pure title compound (25) (2.6 g, 89%) as a white solid
  4. customMS APCI, m/z=439 (M+1), 2.34 min.

Sources & evidence

ORD record
ord-e8f58489f289488eaa66e6d2bfa1fe2b
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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