9-Fluorenylmethyl chloroformate → HCID 86600020, compound

HRID 1097351Notes

Reaction equation

HRID 1097351 reaction equation
Cl.[NH2:2][C@@H:3]([C:5]([NH2:7])=[O:6])[CH3:4].[C:8](Cl)([O:10][CH2:11][CH:12]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9]>C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.O>[NH2:7][C:5](=[O:6])[C@H:3]([NH:2][C:8](=[O:9])[O:10][CH2:11][CH:12]1[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:4]

Participants

6

Reactant 2

HCID 343679-Fluorenylmethyl chloroformateHCID 2775814(2R)-2-Aminopropanamide hydrochloride

Product 1

HCID 86600020HCID 86600020, compoundYield 120.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of D-Alaninamide hydrochloride (3 g) in 10% sodium carbonate solution (50 ml) and dioxan (50 ml) was treated with FMOC chloride (6.24 g) in dioxane (40 ml) and allowed to stir overnight. The mixture was diluted with water (500 ml) and the product collected by filtration and dried in vacuo to give 9.0 g of the subtitle compound.

Workup

  1. filtrationthe product collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-472aa3422020432ab014d4559bf4dd0c
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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