Sodium Carbonate → (9H-Fluoren-9-yl)methyl (2-amino-2-oxoethyl)carbamate

HRID 2075641Notes

Reaction equation

HRID 2075641 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[CH:13]1[C:25]2[CH:24]([CH2:26][O:27][C:28](ON3C(=O)CCC3=O)=[O:29])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][CH:14]=1>CC(C)=O.C(OCC)(=O)C>[CH:13]1[C:25]2[CH:24]([CH2:26][O:27][C:28]([NH:2][CH2:3][C:4]([NH2:6])=[O:5])=[O:29])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 2723639Glycinamide hydrochloride2×

Product 1

HCID 11637939(9H-Fluoren-9-yl)methyl (2-amino-2-oxoethyl)carbamateYield 103.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 2-amino-acetamide hydrochloride (Compound 31, 10.0 g, 90.5 mmol), a 10% aqueous solution of sodium carbonate (600 ml) and acetone (250 ml) were added; next, under ice cooling, a solution of N-(9-fluorenylmethoxycarbonyloxy)succinimide (30.5 mg, 90.5 mmol) in acetone (250 ml) was added drop by drop. After stirring at room temperature for 1 hour, the mixture was concentrated under reduced pressure; the residue obtained was dissolved in ethyl acetate, the organic phase was sequentially washed with a 2N aqueous solution of citric acid, aqueous sodium hydrogen carbonate and saturated brine, after which it was dried with magnesium sulfate. The solid was filtered and concentrated under reduced pressure, after which crystallization from methanol was conducted to yield the desired 2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-acetamide (Compound 32; 27.7 g, quant).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customthe residue obtained
  3. washthe organic phase was sequentially washed with a 2N aqueous solution of citric acid, aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialafter which it was dried with magnesium sulfate
  5. filtrationThe solid was filtered
  6. concentrationconcentrated under reduced pressure
  7. customafter which crystallization from methanol

Sources & evidence

ORD record
ord-ea52397495664adfa8bfb36bf8b4d0c4
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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