Triethylamine → HCID 57803349, compound

HRID 2103375Notes

Reaction equation

HRID 2103375 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:13][CH:12]([C:14]([OH:16])=O)[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.[NH:19]1[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.C(Cl)Cl>[F:17][C:2]([F:1])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:13][CH:12]([C:14]([N:19]3[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH2:20]3)=[O:16])[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 19863007HCID 19863007, compound

Product 1

HCID 57803349HCID 57803349, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[3-(trifluoromethyl)phenyl]-4,5-dihydroisoxazole-5-carboxylic acid (259 mg, 1 mmol) and tert-butyl (3S)-pyrrolidin-3-ylcarbamate (186 mg, 1 mmol) in DMF (0.5 mL) and methylene chloride (5 mL) at 0° C. was added triethylamine (120 mg, 1.2 mmol) and benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate (442 mg, 1 mmol). The mixture was allowed to warm to room temperature over 1 h and stirred at room temperature for 1 h. The mixture was concentrated in vacuo, and the residue was chromatographed on silica gel, eluting with 1% NH4OH in ethyl acetate to give the desired coupling intermediate (410 mg) as a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was chromatographed on silica gel
  3. washeluting with 1% NH4OH in ethyl acetate

Sources & evidence

ORD record
ord-12d7a3ef8bfe4332b51621a5bc707050
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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