Trifluoroacetic acid → Trifluoroacetate

HRID 1290480Notes

Reaction equation

HRID 1290480 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]>>[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

4

Reactant 2

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

Product 2

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

Procedure

Boc-L-Asp(OBzl)-L-Phe-OBzl (9.91 g) was dissolved in a mixture of trifluoroacetic acid (50 ml) and dichloromethanie (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,vbr), 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-76302bd37ec447adbd867c9bea4787c8
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

Loading…