Trimethylsilyl isocyanate → (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid amide

HRID 1006829Notes

Reaction equation

HRID 1006829 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][C@@H:13]([S:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N:39]=[C:40]=[O:41])(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][C@@H:13]([S:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:12][N:11]1[C:40]([NH2:39])=[O:41])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 69427603(2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine

Product 1

HCID 69431348(2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid amideYield 47%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 400 mg (0.86 mmol) (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine in 15 ml CH2Cl2 with 0.3 ml (2.2 mmol) trimethylsilylisocyanate and a catalytic amount of DMAP was stirred over night. The reaction was extracted with aqueous 10% KHSO4/EtOAc (3×) and the organic phase was dried over Na2SO4. Crystallization (CH2Cl2/MeOH/Et2O) gave 205 mg (47%) (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid amide, MS: 509 (MH+).

Workup

  1. extractionThe reaction was extracted with aqueous 10% KHSO4/EtOAc (3×)
  2. dry with materialthe organic phase was dried over Na2SO4
  3. customCrystallization (CH2Cl2/MeOH/Et2O)

Sources & evidence

ORD record
ord-31c3fc6846cd4d178d7d52a4466e1bf2
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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