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

HRID 2165275
Notes
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Reaction equation

HRID 2165275 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 31297Methanesulfonyl chlorideHCID 86744084N2 (t Butyloxycarbonyl)-N-(Phenylmethoxy)-L-threonineamide

Product 1

HCID 86744082N2 (t-Butyloxycarbonyl)-O-(methylsulfonyl)-N-(phenylmethoxy)-L-threonineamid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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

  1. additionwas added dropwise at 0°-5° C
  2. additionwas added
  3. customThe title compound crystallized
  4. filtrationwas filtered off
  5. washwashed with water and petroleum ether
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes