Water → 1-(4-Toluenesulfonyl)-4-(4-toluenesulfonyloxy)-D-proline ethyl ester

HRID 1031561Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[C@H:5]1[CH2:9][CH:8]([OH:10])[CH2:7][N:6]1[S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH3:2].[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.O>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:21])[C@H:5]1[CH2:9][CH:8]([O:10][S:28]([C:25]2[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=2)(=[O:30])=[O:29])[CH2:7][N:6]1[S:11]([C:14]1[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=1)(=[O:12])=[O:13])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold solution of 11.85 g (38 mmoles) 1-(4-toluenesulfonyl)-4-hydroxy-D-proline ethyl ester in 37 mL pyridine at 0° C. was added 8.0 g (41 mmoles) of 4-toluenesulfonyl chloride portionwise in 15 minutes. The cold solution was stirred one hour at 0° C. and then 48 h at room temperature. Water (100 mL) was added dropwise in the solution cooled at 0° C. which was stirred 30 minutes at 0° C. The precipitate was filtered and washed with cold water and ether to give 15.55 g of titled compound. MP 122° C. [α]20 =+26.36° (c=2, chloroform)

Workup

custom48 h
customat room temperature
temperaturecooled at 0° C. which
stirringwas stirred 30 minutes at 0° C
filtrationThe precipitate was filtered
washwashed with cold water and ether

Sources & evidence

ORD record: ord-0dd301ae4814411a8cf21593a58ba239
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04954507

Reaction notes

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