Sodium Bicarbonate → HCID 11190014, compound

HRID 1091250Notes

Reaction equation

HRID 1091250 reaction equation
Cl.CN(C)CCCN=C=NCC.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:23]2[C@@H:27]([C:28]([OH:30])=O)[CH2:26][O:25][CH2:24]2)=[O:22])=[CH:16][CH:15]=1.[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][C:39]2=[O:44])=[CH:34][CH:33]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21]([N:23]2[C@@H:27]([C:28]([NH:31][C:32]3[CH:33]=[CH:34][C:35]([N:38]4[CH2:43][CH2:42][O:41][CH2:40][C:39]4=[O:44])=[CH:36][CH:37]=3)=[O:30])[CH2:26][O:25][CH2:24]2)=[O:22])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111948544-(4-Aminophenyl)morpholin-3-oneHCID 58691300HCID 58691300, compound

Product 1

HCID 11190014HCID 11190014, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.1 1.49 ml (20.0 mmol) of 37% aqueous formaldehyde solution are added to a solution of 2.10 g (20.0 mmol) of D-serine in 10 ml of 1N aqueous sodium hydroxide solution. The resultant solution is left at 5° C. for 18 hours. The solution is heated to 80° C., 6.14 g (40 mmol) of 4-chlorophenyl isocyanate are added, and the mixture is stirred at this temperature for one hour. The mixture is allowed to cool, and the precipitate formed is filtered off. The filtrate is acidified using 1N HCl, and the precipitate formed is filtered off and dried, giving (R)-3-(4-chlorophenylcarbamoyl)oxazolidine-4-carboxylic acid as a colourless solid; ESI 271. 2.2 498 mg (2.60 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) are added to a solution of 541 mg (2.00 mmol) of (R)-3-(4-chlorophenylcarbamoyl)oxazolidine-4-carboxylic acid and 384 mg (2.00 mmol) of 4-(4-aminophenyl)morpholin-3-one in 4 ml of dimethylformamide (DMF), and the mixture is stirred at room temperature for 18 hours. The reaction mixture is added to saturated sodium hydrogencarbonate solution, and the precipitate formed is filtered off, giving 3-N-[(4-chlorophenyl)]-4-N-{[4-(3-oxomorpholin-4-yl)phenyl]}-(R)-oxazolidine-3,4-dicarboxamide (“A2”) as a colourless solid; ESI 461.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off

Sources & evidence

ORD record
ord-cc3bc033628545c3af6da514f2897bfb
Source dataset
uspto-grants-2012_03
Patent number
US08129373B2

Reaction notes

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