Trifluoroacetic acid → Trifluoroacetate

HRID 1291821Notes

Reaction equation

HRID 1291821 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) δ 2.88 (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 (H+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-96a6048fd10549fcbeb11f9106cfac5c
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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