Pyridine → HCID 69432363, compound

HRID 1006820Notes

Reaction equation

HRID 1006820 reaction equation
C(O[C@H]1[CH2:13][C@@H:12]([S:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][N:10]1[CH3:34])C1C=CC=CC=1.Cl[C:36]([O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:37].N1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.Cl.C[CH2:53][O:54][C:55]([CH3:57])=O>C1COCC1>[C:39]1([O:38][C:36]([N:10]2[CH2:11][C@H:12]([S:14][C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:13][C@H:34]2[CH2:53][O:54][CH2:55][C:57]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:37])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 21866389Hydrogen chloride-ethyl acetateHCID 69429841HCID 69429841, compound

Product 1

HCID 69432363HCID 69432363, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.9 g (4.1 mmol) (2S,4R)-2-benzyloxy-methyl-4-tritylsulfanyl-pyrrolidine in 25 ml THF at 0° C. was treated with 0.57 ml (4.5 mmol) phenyl chloroformate and 0.41 ml (5.1 mmol) pyridine. After 2 h at room temperature the reaction was worked up with 1N HCl/EtOAc (3×), the organic phases were washed with H2O, aqueous saturated NaHCO3, dried and evaporated to give 2.6 g (quantitative) (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid phenyl ester, MS: 586 (MH+).

Workup

  1. washthe organic phases were washed with H2O, aqueous saturated NaHCO3
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-3f9e129e75c94cc99cab8e51ff3fa49c
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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