Triethylamine → HCID 86754330, compound

HRID 583434Notes

Reaction equation

HRID 583434 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[C:6]([N:8]([CH:10]([CH:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11][CH2:12][C:13](O)=[O:14])[CH3:9])=[O:7].C(N(CC)CC)C.[NH2:45][C@H:46]([CH2:51][OH:52])[CH2:47][CH:48]([CH3:50])[CH3:49].C(P(=O)(OCC)OCC)#N>CN(C)C=O>[OH:52][CH2:51][C@@H:46]([NH:45][C:13](=[O:14])[CH2:12][CH2:11][CH:10]([N:8]([C:6](=[O:7])[C:5]1[CH:4]=[C:3]([C:2]([F:37])([F:36])[F:1])[CH:31]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:29]=1)[CH3:9])[CH:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:47][CH:48]([CH3:50])[CH3:49]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 111307L-LeucinolHCID 21310523HCID 21310523, compound

Product 1

HCID 86754330HCID 86754330, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 120 mg (0.23 mmol) of 4-[N-(3,5-bistrifluoromethyl-benzoyl)-N-methyl-amino]-5,5-diphenyl-pentanoic acid (example 32 h) and 45 μl (0.32 mmol) of triethylamine in 4 ml of N,N-dimethylformamide at 0° C. is treated with 36 μl (0.28 mmol) of (S)-leucinol, followed by 45 μl (0.28 mmol) of diethyl cyanophosphonate. After stirring for 4 h at room temperature, the reaction mixture is concentrated, diluted with ethyl acetate, and then washed with saturated sodium bicarbonate solution. The aqueous layer is further extracted with ethyl acetate (3×). The organic layers are combined, dried with sodium sulfate and concentrated. The residue is then purified by flash chromatography (98:2 to 95:5 methylene chloride/methanol) to give the title compound as a white solid (mixture of diastereomers). TLC: methylene chloride/methanol (95:5) Rf =0.22, 0.19

Workup

  1. customat 0° C.
  2. concentrationthe reaction mixture is concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution
  5. extractionThe aqueous layer is further extracted with ethyl acetate (3×)
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is then purified by flash chromatography (98:2 to 95:5 methylene chloride/methanol)

Sources & evidence

ORD record
ord-0073fe942b3646f1be0e5f38a9fb8c47
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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