HCID 68688183, compound → HCID 53665853, compound

HRID 1159104Notes

Reaction equation

HRID 1159104 reaction equation
C(OC(=O)[CH2:5][N:6]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:7](=[O:28])[CH:8]([NH:20][C:21](OC(C)(C)C)=[O:22])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)C>C(Cl)Cl.Cl.O1CCOCC1.ClC(Cl)C>[CH2:29]([N:6]1[CH2:5][C:21](=[O:22])[NH:20][C@H:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[C:7]1=[O:28])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 1

HCID 68688183HCID 68688183, compound

Product 1

HCID 53665853HCID 53665853, compoundYield 95.4%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of [benzyl-[2-tert-butoxycarbonylamino-3-(4-trifluoromethyl-phenyl)-propionyl]-amino]-acetic acid ethyl ester (1.5 g, 2.95 mmol) in dry CH2Cl2 (50 mL), 4N HCl in dioxane (25 mL, Aldrich) was added and stirred at room temperature for 2 h and then conc in vacuo. The r×n product was partitioned between CH2Cl2 (100 mL) and saturated NaHCO3 (20 mL). The organic layer was separated, dried over MgSO4 and conc in vacuo to give a clear oil. The oil was diluted in dichloroethane (50 mL) and stirred in 60° C. bath for 2 h to yield 1.02 g (95%) of the product as a off white solid. MS (ESI) 363 (M+H).

Workup

  1. customThe r×n product was partitioned between CH2Cl2 (100 mL) and saturated NaHCO3 (20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4 and conc in vacuo
  4. customto give a clear oil
  5. stirringstirred in 60° C. bath for 2 h

Sources & evidence

ORD record
ord-03deb643c13a40b3ad68ce6fbd1a7a42
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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