Trifluoroacetic acid → HCID 54272787, compound

HRID 412481Notes

Reaction equation

HRID 412481 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][CH:8]([C:18]1[CH:23]=[CH:22][C:21]([NH:24]C(OC(C)(C)C)=O)=[CH:20][CH:19]=1)[NH:9][C:10]([C:12]1[CH:16]=[C:15]([CH3:17])[O:14][N:13]=1)=[O:11])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([O:5][C:6](=[O:32])[CH2:7][CH:8]([C:18]1[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=1)[NH:9][C:10]([C:12]1[CH:16]=[C:15]([CH3:17])[O:14][N:13]=1)=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 538863033-(4-Tert-butoxycarbonylamino-phenyl)-3-[(5-methyl-isoxazole-3-carbonyl)-amino]-propionic acid tert-butyl ester

Product 1

HCID 54272787HCID 54272787, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (R) 3-(4-tert-butoxycarbonylamino-phenyl)-3-[(5-methyl-isoxazole-3-carbonyl)-amino]-propionic acid tert-butyl ester (2 g, Reference Example 11) in dichloromethane (50 mL) was treated with trifluoroacetic acid (5 mL). After four hours [the reaction was monitored by TLC: no more starting material was visible after about 4 hours] at room temperature the reaction mixture was poured carefully onto a mixture of sodium hydrogen carbonate solution (100 mL, 5% w/v) and dichloromethane (50 mL). The organic layer was separated then dried and then evaporated to give the title compound (1.0 g) as a yellow oil which slowly crystallised on standing.

Workup

  1. waitno more starting material was visible after about 4 hours
  2. customThe organic layer was separated
  3. customthen dried
  4. customevaporated

Sources & evidence

ORD record
ord-2847da8ee73547e7bb470155cde7cae1
Source dataset
uspto-grants-2003_05
Patent number
US06562851B2

Reaction notes

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