Ammonia → 2-Amino-2-oxoethyl [4-(1-naphthalenyl-oxy)butyl]carbamate

HRID 912730Notes

Reaction equation

HRID 912730 reaction equation
[C:1]1([O:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]2[C:20](=[O:21])[CH2:19][O:18][C:17]2=[O:22])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH3:23]>O1CCCC1.CO>[C:1]1([O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:22])[O:18][CH2:19][C:20]([NH2:23])=[O:21])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 674163383-[4-(1-Naphthalenyl-oxy)butyl]-1,3-oxazolidine-2,4-dione

Product 1

HCID 111978662-Amino-2-oxoethyl [4-(1-naphthalenyl-oxy)butyl]carbamateYield 46.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.50 g (5.0 mmol) of 3-[4-(1-naphthalenyl-oxy)butyl]-1,3-oxazolidine-2,4-dione, prepared in Step 3.1., are dissolved in a mixture of 10 ml of tetrahydrofuran and 28 ml of a 7N solution of ammonia (200 mmol) in methanol. The solution is left to react overnight at ambient temperature and then evaporated to dryness. The product is purified by chromatography on silica gel, eluting with a 97/3 mixture of dichloromethane and methanol. It is recrystallized from ethyl acetate and then washed with diethyl ether, to give 0.73 g of product in white solid form.

Workup

  1. waitThe solution is left
  2. customto react overnight at ambient temperature
  3. customevaporated to dryness
  4. customThe product is purified by chromatography on silica gel
  5. washeluting with a 97/3 mixture of dichloromethane and methanol
  6. customIt is recrystallized from ethyl acetate
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-5c1e9bb0d10245ae903a69e8bf745dd4
Source dataset
uspto-grants-2011_09
Patent number
US08026258B2

Reaction notes

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