Acetic Acid → HCID 53754612, compound

HRID 1976978Notes

Reaction equation

HRID 1976978 reaction equation
C[O:2][C:3](=[O:34])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]2[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:33])=[O:25])=[CH:19][CH:18]=1)[NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=1[Cl:15])=[O:7].O[Li].O.C(O)(=O)C>C1COCC1.O>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([NH:5][C@H:4]([C:3]([OH:34])=[O:2])[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:24]([C:26]3[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:33])=[O:25])=[CH:21][CH:22]=2)=[O:7])=[C:9]([Cl:15])[CH:10]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 54482344HCID 54482344, compound

Product 1

HCID 53754612HCID 53754612, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[(4-amino-2-chlorophenyl)carbonyl]-4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine methyl ester (66 mg, 0.126 mmol) in THF (3 mL) was treated with a solution of LiOH.H2O (20 mg, 0.48 mmol) in water (0.5 mL) and the mixture was stirred over night at room temperature. Acetic acid (0.5 mL) was added and the mixture was purified directly by RP-HPLC (5-95-35-214) to give 40 mg of a white solid. HRMS: (C23H18Cl3N3O4): Obs. Mass 506.0461. Calcd. Mass 506.0441 (M+H).

Workup

  1. customthe mixture was purified directly by RP-HPLC (5-95-35-214)

Sources & evidence

ORD record
ord-5250198a1acb4fcd9fd14a87ac0fd757
Source dataset
uspto-grants-2001_05
Patent number
US06229011B1

Reaction notes

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