Hydrochloric Acid → Ethyl 3-allyloxycarbonylamino-3-(3-nitrophenyl)-propionate

HRID 1353032Notes

Reaction equation

HRID 1353032 reaction equation
C(N(C(C)C)CC)(C)C.Cl[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12].Cl.[NH2:18][CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=1)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].Cl>C(Cl)Cl>[CH2:14]([O:13][C:11]([NH:18][CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=1)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:12])[CH:15]=[CH2:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 18052Allyl chloroformateHCID 81531DiisopropylethylamineHCID 16188861Ethyl 3-amino-3-(3-nitrophenyl)propanoate hydrochloride

Product 1

HCID 21101502Ethyl 3-allyloxycarbonylamino-3-(3-nitrophenyl)-propionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (66 ml) and allyl chloroformate (22 ml) in 150 ml of methylene chloride were added at 0° C. to a solution of ethyl 3-amino-3-(3-nitrophenyl)-propionate hydrochloride from II.1b (47 g) in 350 ml of methylene chloride. After a reaction time of 30 min, HCl (1N, 100 ml) was added. The organic phase was separated off, washed with water, dried over MgSO4 and concentrated. A white solid was obtained (yield: 56.4 g).

Workup

  1. customThe organic phase was separated off
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customA white solid was obtained (yield: 56.4 g)

Sources & evidence

ORD record
ord-cf44187c2a03441392832fe49adac901
Source dataset
uspto-grants-2007_05
Patent number
US07220824B1

Reaction notes

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