HCID 57101340, compound → HCID 56978043, compound

HRID 1982638Notes

Reaction equation

HRID 1982638 reaction equation
CC(C)([O:4][C:5](=[O:35])[CH2:6][O:7][CH2:8][CH:9]([NH:17][C:18]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C>FC(F)(F)C(O)=O>[C:5]([CH2:6][O:7][CH2:8][CH:9]([NH:17][C:18]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([OH:35])=[O:4]

Participants

3

Reactant 1

HCID 57101340HCID 57101340, compound

Product 1

HCID 56978043HCID 56978043, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(2S)-Phenylmethyl 2-[[[1-[[2-(1,1-dimethylethoxy)-2-oxoethoxy]methyl]-2-phenylethyl]amino]carbonyl]-1-pyrrolidinecarboxylate (side chain in 2 position is (±) mixture), 0.5 g (0.0010 mol), is dissolved in 30 ml of trifluoroacetic acid at 0° C. The mixture is allowed to stand 30 minutes at 0° C. and then allowed to reach room temperature over one hour and the solvent evaporated in vacuo at 25° C. The residue is dissolved in 100 ml of dichloromethane and washed with a saturated aqueous solution of sodium chloride, 2×100 ml. The dichloromethane layer is separated, dried over sodium sulfate, evaporated in vacuo, and the residue purified by chromatography using silica gel and eluting with dichloromethane methanol (95:5) to give (2S)-phenylmethyl 2-[[[1-[(carboxymethoxy)methyl]-2-phenylethyl]amino]carbonyl]-1-pyrrolidinecarboxylate (center on chain in 2 position is a mixture of isomers), 0.39 g; [α]D25 -52.2° (c 0.23, methanol).

Workup

  1. waitto reach room temperature over one hour
  2. customthe solvent evaporated in vacuo at 25° C
  3. dissolutionThe residue is dissolved in 100 ml of dichloromethane
  4. washwashed with a saturated aqueous solution of sodium chloride, 2×100 ml
  5. customThe dichloromethane layer is separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customthe residue purified by chromatography
  9. washeluting with dichloromethane methanol (95:5)

Sources & evidence

ORD record
ord-398a735d01ef4394915998369ccdf94f
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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