Acetyl chloride → HCID 70032690, compound

HRID 431837Notes

Reaction equation

HRID 431837 reaction equation
[F:1][C:2]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:3]=1[CH2:4][NH:5][CH2:6][C@@H:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][N:8]1[C:32]1[N:37]=[CH:36][C:35]([CH2:38][CH2:39][CH3:40])=[CH:34][N:33]=1.[C:46](Cl)(=[O:48])[CH3:47]>N1C=CC=CC=1>[F:1][C:2]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:3]=1[CH2:4][N:5]([CH2:6][C@@H:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:9][N:8]1[C:32]1[N:33]=[CH:34][C:35]([CH2:38][CH2:39][CH3:40])=[CH:36][N:37]=1)[C:46](=[O:48])[CH3:47]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 11479096HCID 11479096, compound

Product 1

HCID 70032690HCID 70032690, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

160 mg (0.258 mmol) (2S,4R)-(2,5-Difluoro-benzyl)-[1-(5-propyl-pyrimidin-2-yl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-amine in 2 ml pyridine were treated with 37 μl (0.52 mmol) acetyl chloride at 0° C. The solution was stirred at RT for 1.5 h, poured on ice water and was extracted with EtOAc. The combined organic layers were washed with 1N HCl and brine, dried over Na2SO4 and were evaporated. Column chromatography with EtOAc:hexane 1:2 to 1:1 yielded 170 mg (quant) (2S,4R)-N-(2,5-Difluoro-benzyl)-N-[1-(5-propyl-pyrimidin-2-yl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-acetamide as white foam.

Workup

  1. additionpoured on ice water
  2. extractionwas extracted with EtOAc
  3. washThe combined organic layers were washed with 1N HCl and brine
  4. dry with materialdried over Na2SO4
  5. customwere evaporated

Sources & evidence

ORD record
ord-be1f53f97abe4c7aa2d9125a4452b61d
Source dataset
uspto-grants-2003_12
Patent number
US06660738B2

Reaction notes

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