Trifluoroacetic acid → Trifluoroacetate

HRID 864785Notes

Reaction equation

HRID 864785 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:14]([NH:16][C@H:17]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>ClCCl>[NH2:1][C@H:2]([C:14]([NH:16][C@H:17]([C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:15])[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1.[F:42][C:43]([F:48])([F:47])[C:44]([O-:46])=[O:45]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10437796Boc-L-Asp(OBzl)-L-Phe-OBzl

Product 2

HCID 84468TrifluoroacetateHCID 10004433L-Asp(OBzl)-L-Phe-OBzl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boc-L-Asp(OBzl)-L-Phe-OBzl (9.91 g) was dissolved in a mixture of trifluoroacetic acid (50 ml) and dichloromethane (50 ml). The resultant solution was stored at room temperature for 2 hr. The reaction mixture was evaporated to dryness to yield a residue which was triturated with ether, collected, washed thoroughly with ether and dried under high vacuum to yield L-Asp(OBzl)-L-Phe-OBzl, trifluoroacetate salt (8.36 g) as a white solid: NMR (CDCl3) δ2.88 (2H, m), 3.07 (2H, m), 4.33 (1H, m), 4.78 (1H, m), 5.02 (2H, s), 5.06 (2H, q), 6.20 (3H, v. br), 7.04 (2H, m), 7.26 (13H, m), 7.65 (1H, d); m/Z 461 (M +H)+.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customto yield a residue which
  3. customwas triturated with ether
  4. customcollected
  5. washwashed thoroughly with ether
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-bf38199413a649d99841cecc956ed43d
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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