Trifluoroacetic acid → 4-(2-N-benzyloxycarbonyl-L-valyloxyethoxy)-benzoic acid

HRID 989990Notes

Reaction equation

HRID 989990 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:39]=[CH:38][C:25]([C:26]([O:28]CC2C=CC(OC)=CC=2)=[O:27])=[CH:24][CH:23]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.ICC1C=C(OCCOC(=O)[C@H](C(C)C)NC(OCC2C=CC=CC=2)=O)C=CC=1C(O)=O>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:39]=[CH:38][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 23387399iodomethyl 4-(2-N-benzyloxycarbonyl-L-valyloxyethoxy)-benzoic acidHCID 233875454-methoxybenzyl 4(2-N-benzyloxycarbonyl-L-valyloxyethoxy)benzoate

Product 1

HCID 233875344-(2-N-benzyloxycarbonyl-L-valyloxyethoxy)-benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxybenzyl 4(2-N-benzyloxycarbonyl-L-valyloxyethoxy)benzoate (10.2 g, 19.04 mmole) in dichloromethane (100 ml) was added trifluoroacetic acid (20 ml) and the mixture was stirred 3 hours at room temperature. The solution was evaporated under reduced pressure and co-evaporated two times with toluene. The product was isolated by silica gel column chromatography. Yield: 6.9 g=87%. The product may be activated and esterified direct to a drug or converted to iodomethyl 4-(2-N-benzyloxycarbonyl-L-valyloxyethoxy)-benzoic acid as described above, that is by treatment with a base, chloroiodomethane, separation and then treatment with NaI.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. customThe product was isolated by silica gel column chromatography
  3. customthat is by treatment with a base, chloroiodomethane, separation

Sources & evidence

ORD record
ord-3852e86374db4389a3fe2c0b3ba3d9cc
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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