Hydrochloric Acid → N2 (t-Butyloxycarbonyl)-O-(methylsulfonyl)-N-(phenylmethoxy)-L-threonineamid

HRID 2165275Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

N2 -(t Butyloxycarbonyl)-N-(Phenylmethoxy)-L-threonineamide (244 g) was dissolved in 1.2 liters of pyridine and the solution was cooled to 0° C. With stirring 120 grams of methanesulfonyl chloride was added dropwise at 0°-5° C. After 2.5 hours, the reaction mixture was poured into a mixture of 1500 ml of 2N hydrochloric acid and ice and concentrated HCl was added to adjust the pH of the mixture to 4. The title compound crystallized, and, after stirring for 1 hour, was filtered off, washed with water and petroleum ether. After drying at room temperature the yield was 356.4 grams, which contained a considerable amount of water, melting point 128°-130° C. dec.

Workup

additionwas added dropwise at 0°-5° C
additionwas added
customThe title compound crystallized
filtrationwas filtered off
washwashed with water and petroleum ether
customAfter drying at room temperature the yield was 356.4 grams, which

Sources & evidence

ORD record: ord-c89acd800449493fa6d216845b4402ad
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04939253

Reaction notes

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