1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-[2-(4-Bromophenyl)-2-hydroxy-propyl]-3-hydroxy-2,5-dioxopyrrolidin-3-ylacetic acid, ethyl ester

HRID 743725Notes

Reaction equation

HRID 743725 reaction equation
Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[OH:24][C:25]([C:36]([O:38]CC)=O)([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:26][C:27]([OH:29])=O.[NH2:41][CH2:42][C:43]([C:46]1[CH:51]=[CH:50][C:49]([Br:52])=[CH:48][CH:47]=1)([OH:45])[CH3:44]>C1COCC1.C(N(CC)CC)C.C(Cl)Cl>[Br:52][C:49]1[CH:48]=[CH:47][C:46]([C:43]([OH:45])([CH3:44])[CH2:42][N:41]2[C:27](=[O:29])[CH2:26][C:25]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])([OH:24])[C:36]2=[O:38])=[CH:51][CH:50]=1

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 15384083Diethyl CitrateHCID 194246941-Amino-2-(4-bromophenyl)propan-2-ol

Product 1

HCID 702050181-[2-(4-Bromophenyl)-2-hydroxy-propyl]-3-hydroxy-2,5-dioxopyrrolidin-3-ylacetic acid, ethyl esterYield 28%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (0.833 g, 4.34 mmol) followed by 1-hydroxybenzotriazole hydrate (0.66 g, 4.35 mmol), 3-hydroxy-3,4-bis (ethoxycarbonyl)butanoic acid (1.08 g, 4.35 mmol) in THF (50 ml) and triethylamine is added to a stirred solution of 1-amino-2-(4-bromophenyl) propan-2-ol (Preparation 19, 1 g, 4.35 mmol) in THF (45 ml). The reaction mixture is stirred at ambient temperature for 18 hrs, diluted with CH2Cl2 and washed with saturated NaHCO3 solution followed by saturated NaCl solution. The organic layer is dried over MgSO4, concentrated and purified by flash chromatography (2% MeOH/CH2Cl2) to give 1-[2-(4-bromophenyl)-2-hydroxy-propyl]-3-hydroxy-2,5-dioxopyrrolidin-3-ylacetic acid, ethyl ester (0.5 g, 28% yield); MS (FAB+ion) m/z 414/416 (M+H)+ and 4-[2-(4-bromophenyl)-2-hydroxypropylcarbamoyl]-3-hydroxy-3-methyl butyric acid ethyl ester (0.94 g, 50% yield); MS (FAB+ion) m/z 460/462 (M+H)+.

Workup

  1. washwashed with saturated NaHCO3 solution
  2. dry with materialThe organic layer is dried over MgSO4
  3. concentrationconcentrated
  4. custompurified by flash chromatography (2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4199f89eb52143f6935c6a819d62f118
Source dataset
uspto-grants-1996_09
Patent number
US05556990

Reaction notes

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