9-Fluorenylmethyl chloroformate → 9-Fluorenylmethyl carbamate

HRID 243605Notes

Reaction equation

HRID 243605 reaction equation
C([NH:4]CC1SC=C(CN2CCN([C@@H]([C@@H](C)CC)C(OC(C)(C)C)=O)C2=O)N=1)(C)C.C([O-])(O)=O.[Na+].Cl[C:36]([O:38][CH2:39][CH:40]1[C:52]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[C:46]2[C:41]1=[CH:42][CH:43]=[CH:44][CH:45]=2)=[O:37]>C(#N)C.O>[C:36]([NH2:4])([O:38][CH2:39][CH:40]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:46]2[C:41]1=[CH:42][CH:43]=[CH:44][CH:45]=2)=[O:37]

Participants

6

Reactant 3

HCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 66889849tert-butyl (2S,3S)-2-[3-({2-[(isopropylamino)methyl]-1,3-thiazol-4-yl}methyl)-2-oxo-1-imidazolidinyl]-3-methylpentanoate

Product 1

HCID 7363019-Fluorenylmethyl carbamateYield 141.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of the product of Example 283A (59 mg) in acetonitrile (0.9 mL) and water (0.3 mL) was treated with NaHCO3 (34 mg, 2.4 equivalents) followed by 9-fluorenylmethyl chloroformate (53 mg, 1.2 equivalents) at 25° C. for 1.5 h. The solvents were evaporated and the residue was purified using ethyl acetate:chloroform (1:4) to give 47 mg (40%) of FMOC-amine which was dissolved in dichloromethane (0.5 mL) and trifluoroacetic acid (0.5 mL) and stirred at 25° C. for 1 h. The solvents were evaporated, and the acid was used directly for the next step.

Workup

  1. customThe solvents were evaporated
  2. customthe residue was purified

Sources & evidence

ORD record
ord-2f61eaaf3503441cab16b3df9a7a4e79
Source dataset
uspto-grants-2014_02
Patent number
US08653141B2

Reaction notes

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