Benzyl chloroformate → HCID 59369842, compound

HRID 1662097Notes

Reaction equation

HRID 1662097 reaction equation
CC1S[C:4]([C:10]2[CH:15]=CC=C[CH:11]=2)=[C:5]([C:7]([OH:9])=O)[N:6]=1.C(N(C(C)C)CC)(C)C.[C:25](Cl)([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>ClCCl>[OH:9][CH2:7][C@H:5]1[N:6]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH2:11][C@@H:10]2[C@H:4]1[CH2:15]2

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 9435352-methyl-5-phenyl-1,3-thiazole-4-carboxylic Acid

Product 1

HCID 59369842HCID 59369842, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of racemic 7-1 (7.2 g, 63.6 mmol, synthesized as in Example 1) in dichloromethane (320 mL) at 0° C. was added diisopropylethylamine (10.7 g, 83.0 mmol) followed by CbzCl (11.9 g, 70.0 mmol) and the reaction mixture was slowly warmed to ambient temperature over 48 h. The mixture was then quenched with water and extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to an oil. The oil was purified by normal phase silica gel chromatography (0 to 100% EtOAc in hexanes) to afford the product as an oil. ESI+ MS: [M+H]+ 248.3.

Workup

  1. customThe mixture was then quenched with water
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated to an oil
  5. customThe oil was purified by normal phase silica gel chromatography (0 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4cb85c0c9e7843bfba00139727e7958f
Source dataset
uspto-grants-2011_10
Patent number
US08030495B2

Reaction notes

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