Tributylphosphine → HCID 68561694, compound

HRID 20381Notes

Reaction equation

HRID 20381 reaction equation
[C:1]([O:5][C:6](=[O:56])[N:7]([C@H:19]([CH2:54][OH:55])[C@@H:20]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C@@H:21]([N:31]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=1)[CH2:8][C@@H:9](O)[CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].C(P(CCCC)CCCC)CCC>C1C=CC=CC=1>[C:1]([O:5][C:6]([N:7]1[C@@H:19]([C@@H:20]([O:46][CH2:47][C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[C@@H:21]([N:31]([CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:22][C:23]2[CH:24]=[C:25]([F:30])[CH:26]=[C:27]([F:29])[CH:28]=2)[CH2:54][O:55][C@@H:9]([CH2:10][O:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:8]1)=[O:56])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 13831TributylphosphineHCID 68561132HCID 68561132, compound

Product 1

HCID 68561694HCID 68561694, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Dissolve [(1R,2S,3S)-2-benzyloxy-3-dibenzylamino-4-(3,5-difluorophenyl)-1-hydroxymethyl-butyl]-((R)-3-cyclohexyloxy-2-hydroxypropyl)-carbamic acid tert-butyl ester (0.940 g, 1.216 mmol) in benzene (6 mL) followed by the addition of tributylphosphine (0.369 g, 1.824 mmol) and N,N-tetramethyl azodicarboxamide (TMAD) (0.314 g, 1.824 mmol). Stir vigorously for 16 hours, filter the slurry, wash with hexanes and purify (silica gel chromatography, eluting with 5:95 to 15:85 ethyl acetate:hexanes) to give the desired compound as a white foam (0.777 g, 84.7%).

Workup

  1. filtrationfilter the slurry
  2. washwash with hexanes
  3. custompurify
  4. wash(silica gel chromatography, eluting with 5:95 to 15:85 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-12ed992592f94c218cb5ba2fe9f15392
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

Loading…