9-Fluorenylmethyl chloroformate → HCID 67335727, compound

HRID 335377Notes

Reaction equation

HRID 335377 reaction equation
[NH2:1][C:2]1[C:3]2[NH:10][CH:9]=[C:8]([CH2:11][NH:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])[C:4]=2[N:5]=[CH:6][N:7]=1.[C:18](Cl)([O:20][CH2:21][CH:22]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19]>CO.C([O-])(O)=O.[Na+]>[NH2:1][C:2]1[C:3]2[NH:10][CH:9]=[C:8]([CH2:11][N:12]([CH:13]([CH2:14][OH:15])[CH2:16][OH:17])[C:18](=[O:19])[O:20][CH2:21][CH:22]3[C:34]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:28]4[C:23]3=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 343679-Fluorenylmethyl chloroformateHCID 67334826HCID 67334826, compound

Product 1

HCID 67335727HCID 67335727, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Amine 6 (330 mg, 1.4 mmol) was suspended in methanol (35 mL) and 10% aqueous NaHCO3 (3.5 mL). Fmoc chloride (432 mg, 1.7 mmol) was added and the solution stirred for 15 min. The suspension was concentrated under reduced pressure. Chromatography of the residue on a column of silica gel eluted with 7.5-20% methanol in dichloromethane gave the title compound 7 (150 mg, 0.33 mmol, 48% allowing for recovered starting material). Subsequent elution with 50% methanolic ammonia (3.5M) in dichloromethane returned the starting amine 6 (170 mg, 51%). 7, colourless amorphous solid, ESI-MS+, found 460.1975, calc. for C25H26N5O5 [M+H]+ 460.1985.

Workup

  1. concentrationThe suspension was concentrated under reduced pressure
  2. washChromatography of the residue on a column of silica gel eluted with 7.5-20% methanol in dichloromethane

Sources & evidence

ORD record
ord-42bd6ba3416147cba819f717bb855a43
Source dataset
uspto-grants-2014_11
Patent number
US08884000B2

Reaction notes

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