Acetic Acid → HCID 86756663, compound

HRID 1976241Notes

Reaction equation

HRID 1976241 reaction equation
[OH:1][C@H:2]1[CH2:37][N:5]2[C:6]3[C:11]([N:12]([C:14](=[O:36])[C:15]4[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:35])[C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=5[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:17][CH:16]=4)[CH2:13][C@@H:4]2[CH2:3]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[C:38](O)(=[O:40])[CH3:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[C:38]([O:1][C@@H:2]1[CH2:37][N:5]2[C:6]3[C:11]([N:12]([C:14](=[O:36])[C:15]4[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:35])[C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=5[C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)=[CH:19][CH:20]=4)[CH2:13][C@@H:4]2[CH2:3]1)=[CH:10][CH:9]=[CH:8][CH:7]=3)(=[O:40])[CH3:39]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 15545387HCID 15545387, compound

Product 1

HCID 86756663HCID 86756663, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2R,3aS)-2-hydroxy-5-[4-[(2-phenylbenzoyl)amino]benzoyl]-1,2,3,3a,4,5-hexahydro-pyrrolo[1,2-a]quinoxaline (0.8 g) prepared in Example 3, acetic acid (0.15 g) and triphenyl phosphine (0.64 g) in anhydrous tetrahydrofuran (5 ml), there was gradually dropwise added a solution of diisopropyl azodicarboxylate (0.49 g) in anhydrous tetrahydrofuran (2 ml) under ice-cooling. After stirring the reaction solution at room temperature for 2 hours, it was concentrated. The resulting residue was subjected to silica gel column chromatography and then eluted with hexane/ethyl acetate (1/1) to give 0.66 g (yield 76.0%) of the title compound as amorphous powder.

Workup

  1. temperaturecooling
  2. concentrationit was concentrated
  3. washeluted with hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-f50b9e06289744599a4464c3b11b2af3
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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