1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → HCID 57311781, compound

HRID 980237Notes

Reaction equation

HRID 980237 reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:16][C:17]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](O)=[O:20]>C(Cl)Cl.CN1CCOCC1.ClC(OCC(C)C)=O>[O:20]=[C:19]1[C:18]2[CH:22]=[CH:23][CH:24]=[C:25]([C:26]([F:27])([F:28])[F:29])[C:17]=2[N:16]=[C:10]([C@@H:9]2[CH2:13][CH2:14][CH2:15][N:8]2[C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[O:12]1

Participants

6

Reactant 2

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 6045692-Amino-3-(trifluoromethyl)benzoic acid

Product 1

HCID 57311781HCID 57311781, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent3×HCID 79724-MethylmorpholineSolvent2×HCID 62365Isobutyl chloroformateSolvent

Procedure

Using the procedure of Step A of Example 7, a solution of 16.14 ml of BOC-L-proline in 150 ml of methylene chloride, 20.6 ml of N-methyl-morpholine, 19.5 ml of isobutyl chloroformate in 75 ml of methylene chloride and 15.4 g of 2-amino-3-trifluoromethylbenzoic acid in 150 ml of methylene chloride and 8.3 ml of N-methyl-morpholine were reacted for 20 hours. The mixture was extracted with methylene chloride and the residue was chromatographed on silica gel and was eluted with methylene chloride to obtain 16.4 g of 1,1-dimethylethyl (2S) 2-[4-oxo-8-(trifluoromethyl)-4H-3,1-benzoxazin-2-yl]-1-pyrrolidine carboxylate having a specific rotation of [α]D =-75°±2.5° (c=0.6% in CH3COOH).

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. customthe residue was chromatographed on silica gel
  3. washwas eluted with methylene chloride

Sources & evidence

ORD record
ord-b472a7262ceb4ffea013559ecf82b822
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

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