Trimethylphosphine → HCID 70076632, compound

HRID 1872461Notes

Reaction equation

HRID 1872461 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH2:8][C@@H:9]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@@:10]2([N:22]=[N+]=[N-])[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:5])[CH3:2].P(C)(C)C>C1COCC1.O.CCOCC>[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH2:8][C@@H:9]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C@@:10]2([NH2:22])[C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 68983TrimethylphosphineHCID 86755671(1S,2R,3R,5R,6S)-2-azido-3-benzyloxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Product 1

HCID 70076632HCID 70076632, compoundYield 51.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1S,2R,3R,5R,6S)-2-azido-3-benzyloxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XXIII-3) (120 mg, 0.276 mmol) in THF (4 mL) and H2O (0.4 mL) was added Me3P (0.30 mL, 0.30 mmol, 1 M sol. in THF) and stirring was continued at 23° C. for 4 h. The reaction mixture was diluted with ether, washed with sat. NaHCO3 -sol., brine and dried over Na2SO4. The crude product was purified by silica gel column chromatography with hexane/EtOAc 1:1 (+small amount of Et3N) to give (1S,2R,3R,5R,6S)-2-amino-3-benzyloxy-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XXIV-3) (58 mg, 51%) as a yellow oil. 1H-NMR (250 MHz, CDCI3) □1.23 (3H, t, J=7.1 Hz), 1.72 (1H, t, J=3.5 Hz), 1.93 (2H, bs), 2.00 (1H, m), 2.10 (1H, dd, J=7, 3.5 Hz), 2.19 (1H, m), 2.27 (1H, dd,J=12,7 Hz), 3.46 (1H, dd,J=8, 7 Hz), 4.10 (2H, q,J=7.1 Hz), 4.47 (2H, s),5.20 (1H,d,J=12 Hz), 5.30 (1H, d,J=12 Hz), 7.18-7.42 (10H,m);MS[ISP] 410 [(M+H)+ ]; □D20 +3.54° (c=0.90, CHCl3).

Workup

  1. washwashed with sat. NaHCO3 -sol
  2. dry with material, brine and dried over Na2SO4
  3. customThe crude product was purified by silica gel column chromatography with hexane/EtOAc 1:1 (+small amount of Et3N)

Sources & evidence

ORD record
ord-bcd18d0c75b54f54b7a82b940db5b590
Source dataset
uspto-grants-2000_08
Patent number
US06107342

Reaction notes

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