Trifluoroacetic acid → (2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl-(1H-tetrazol-5-ylmethyl)-amide

HRID 1264403Notes

Reaction equation

HRID 1264403 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:18][C@H:17]([S:19]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:16][C@H]1C(O)=O)(=[O:13])=[O:12].COC1C=CC(C[N:49]2[N:53]=[N:52][C:51]([CH2:54][N-:55][CH3:56])=[N:50]2)=CC=1.C([SiH](CC)CC)C.[C:66](O)([C:68](F)(F)F)=[O:67]>>[CH3:56][N:55]([CH2:54][C:51]1[NH:52][N:53]=[N:49][N:50]=1)[C:66]([C@@H:68]1[CH2:16][C@@H:17]([SH:19])[CH2:18][N:14]1[S:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)(=[O:12])=[O:13])=[O:67]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 69428772(2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acidHCID 86758903[2-(4-methoxy-benzyl)-2H-tetrazol-5-ylmethyl]-methyl-amide

Product 1

HCID 178483115(2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl-(1H-tetrazol-5-ylmethyl)-amideYield 57%

Conditions

Temperature
80 °C

Procedure

A solution of 150 mg (0.19 mmol) of a 1:1 mixture of (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid [1-(4-methoxy-benzyl)-1H- and [2-(4-methoxy-benzyl)-2H-tetrazol-5-ylmethyl]-methyl-amide in 10 ml TFA was treated with 0.3 ml (1.9 mmol) triethylsilane, refluxed for 7 min at 80° C. and evaporated. Crystallization from CH2Cl2/Et2O gave 46 mg (57%) (2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl-(1H-tetrazol-5-ylmethyl)-amide, mp: 175 slow dec., MS: 433 (MH+).

Workup

  1. customevaporated
  2. customCrystallization from CH2Cl2/Et2O

Sources & evidence

ORD record
ord-affd5dd3860148ed8807b247c9b972a1
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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