Trifluoroacetic acid → D-Phe-Pro-OBn.TFA

HRID 1416576Notes

Reaction equation

HRID 1416576 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:10]([N:12]1[CH2:26][CH2:25][CH2:24][C@H:13]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(OC)C=CC=CC=1.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>ClCCl>[NH2:1][C@@H:2]([C:10]([N:12]1[CH2:26][CH2:25][CH2:24][C@H:13]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:42][C:43]([C:44]([OH:46])=[O:45])([F:48])[F:47]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 11155205Boc-(D)Phe-Pro-OBzl

Product 1

HCID 131720381D-Phe-Pro-OBn.TFAYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of Boc-D-Phe-Pro-OBn (68 g, 150 mmol) in dichloromethane (50 mL) at 0° C., was added anisole (20 mL) followed by trifluoroacetic acid (400 mL). After stirring for 3 hours, the solvents were evaporated in vacuo and the thick oily residue was dissolved in diethyl ether (1.5 L) and refrigerated (72 hours). The white precipitate was filtered, washed with diethyl ether (300 mL) and dried to yield 59.4 g (85%) of white powder.

Workup

  1. customthe solvents were evaporated in vacuo
  2. dissolutionthe thick oily residue was dissolved in diethyl ether (1.5 L)
  3. custom(72 hours)
  4. filtrationThe white precipitate was filtered
  5. washwashed with diethyl ether (300 mL)
  6. customdried

Sources & evidence

ORD record
ord-c8617a70bdbf4897a3b485387dc888da
Source dataset
uspto-grants-1999_06
Patent number
US05914319

Reaction notes

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