Trifluoroacetic acid → HCID 57172084, compound

HRID 1602982Notes

Reaction equation

HRID 1602982 reaction equation
C(OC(C[N:9]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)(=[O:20])=[O:19])[C@@H:10]([C:15]([OH:17])=[O:16])[C:11]([SH:14])([CH3:13])[CH3:12])=O)(C)(C)C.F[C:36](F)(F)[C:37]([OH:39])=[O:38]>ClCCl>[C:37]([CH2:36][S:14][C:11]([CH3:13])([CH3:12])[C@H:10]([C:15]([OH:17])=[O:16])[NH:9][S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)(=[O:19])=[O:20])([OH:39])=[O:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131721449HCID 131721449, compound

Product 1

HCID 57172084HCID 57172084, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of S--(t-Butoxycarbonyl)methyl--N--[4-(4-fluorophenoxy)benzenesulfonyl]-D-penicillamine (188.8 mg, 0.367 mmol) in 3.4 mL of dichloromethane at 20° C. was added trifluoroacetic acid (0.85 mL). The solution was stirred for 16 h and concentrated in vacuo. The residue was partitioned between ethyl acetate (25 mL) and 1 M aq. phosphate buffer (pH 7). The aqueous layer was extracted with two additional portions of ethyl acetate (25 mL), and the combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The residue was triturated with diethyl ether (5 mL) to give 67 mg (40%) of S-Carboxymethyl--N--[4-(4-fluorophenoxy)benzenesulfonyl]-D-penicillamine as an off-white solid: mp 69° C.; 1H--NMR (DMSO-d6) δ 1.32 (br s, 6H), 3.25-3.5 (br m, 3H), 7.12 (d, J=8 Hz, 2H), 7.2-7.5 (m, 4H), 7.82 (d, J=8 Hz, 2H), 8.00-8.40 (br s, 1H), 12.5-13.2 (v br s, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate (25 mL) and 1 M aq. phosphate buffer (pH 7)
  3. extractionThe aqueous layer was extracted with two additional portions of ethyl acetate (25 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was triturated with diethyl ether (5 mL)

Sources & evidence

ORD record
ord-829fd7d1c7224b6fb398d93dbd2ac51a
Source dataset
uspto-grants-1999_11
Patent number
US05985900

Reaction notes

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