4-Toluenesulfonyl chloride → cis-N-Carbobenzyloxy-4-tosyloxy-L-proline, methyl ester

HRID 1733350Notes

Reaction equation

HRID 1733350 reaction equation
[C:1]([N:11]1[CH2:19][C@@H:18]([OH:20])[CH2:17][C@H:12]1[C:13]([O:15][CH3:16])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>N1C=CC=CC=1>[C:1]([N:11]1[CH2:19][C@@H:18]([O:20][S:21]([C:24]2[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:17][C@H:12]1[C:13]([O:15][CH3:16])=[O:14])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 688413(2S,4S)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 14036189cis-N-Carbobenzyloxy-4-tosyloxy-L-proline, methyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following the procedure of Example 19(b), the methyl ester product from part (b) is treated with 12.4 g. of tosyl chloride in 45 ml. of pyridine to give 13.2 g. of cream-colored product; m.p. 114°-117° (s. 105°). 13 g. of this material are recrystallized from 70 ml. of ethanol to 8.4 g. of colorless cis-N-carbobenzyloxy-4-tosyloxy-L-proline, methyl ester; m.p. 133°-135°; [α]D25 -26° (c=1%, chloroform).

Workup

  1. customm.p. 114°-117° (s. 105°)
  2. customof this material are recrystallized from 70 ml

Sources & evidence

ORD record
ord-291d7a927ed04c2781925f8e6d809f78
Source dataset
uspto-grants-1980_12
Patent number
US04241076

Reaction notes

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