Benzyl chloroformate → HCID 58746644, compound

HRID 724743Notes

Reaction equation

HRID 724743 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[S:24](=[O:26])(=[O:25])[N:23]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:22](=[O:31])[CH2:21]2)=[CH:16][CH:15]=1)[C:10]([NH2:12])=[O:11].C(N(CC)C(C)C)(C)C.Cl[C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43]>O1CCCC1.O>[CH2:45]([O:44][C:42](=[O:43])[NH:8][C@H:9]([C:10](=[O:11])[NH2:12])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]2[S:24](=[O:26])(=[O:25])[N:23]([C:27]([CH3:28])([CH3:30])[CH3:29])[C:22](=[O:31])[CH2:21]2)=[CH:18][CH:19]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 69597827HCID 69597827, compound

Product 1

HCID 58746644HCID 58746644, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-2-amino-3-[4-(2-tert-butyl-1,1,3-trioxo-1λ6-isothiazolidin-5-yl)-phenyl]-propionamide trifluoroacetate (600 mg, 1.5 mmol) and N,N-diisopropylethylamine (540 μL, 3.1 mmol) in tetrahydrofuran (7.6 mL) was cooled to 0° C. and treated with benzyl chloroformate (250 μL, 1.7 mmol). The reaction mixture was stirred for 2 h, diluted with water (20 mL), and extracted with ethyl acetate (60 mL). The organic layer was dried with Na2SO4, filtered, and concentrated to give a solid which was purified using flash column chromatography (10% methanol/dichloromethane) to yield the desired product (720 mg, 96%). LCMS found for C24H30N3O6S (M+H)+: m/z=488.

Workup

  1. extractionextracted with ethyl acetate (60 mL)
  2. dry with materialThe organic layer was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a solid which
  6. customwas purified

Sources & evidence

ORD record
ord-05b2e38c0c75408c8a0570cd07f3a658
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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