Citric Acid → HCID 86592733, compound

HRID 2251912Notes

Reaction equation

HRID 2251912 reaction equation
CN1CCOCC1.[N:8]1([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([N:22]3[CH2:29][CH2:28][CH2:27][C@@H:23]3[C:24]([OH:26])=O)=[O:21])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1.ClC(OCC)=O.Cl.[Br:37][C:38]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:39]=1[CH2:40][O:41][C:42]1[CH:48]=[CH:47][CH:46]=[CH:45][C:43]=1[NH2:44].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1.O>[Br:37][C:38]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:39]=1[CH2:40][O:41][C:42]1[CH:48]=[CH:47][CH:46]=[CH:45][C:43]=1[NH:44][C:24]([C@H:23]1[CH2:27][CH2:28][CH2:29][N:22]1[C:20](=[O:21])[CH2:19][C:16]1[CH:15]=[CH:14][C:13]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)=[CH:18][CH:17]=1)=[O:26]

Participants

8

Reactant 5

HCID 311Citric AcidHCID 79724-Methylmorpholine2×HCID 10928Ethyl chloroformateHCID 22934172HCID 22934172, compoundHCID 57426176HCID 57426176, compound

Product 1

HCID 86592733HCID 86592733, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

Toluene (37.8 ml) and N-methylmorpholine (1.10 g, 10.8 mmol) were added to N-[(4-pyrrolidinophenyl)acetyl]-D-proline (2.90 g, 9.59 mmol). Ethyl chloroformate (1.14 g, 10.5 mmol) was added to the obtained mixture in an ice bath, and they were stirred for 2 hours. 2-(2-Bromo-5-fluorobenzyloxy)aniline hydrochloride (3.19 g, 9.59 mmol) and N-methylmorpholine (1.16 g, 11.5 mmol) were added thereto and the temperature of the obtained mixture was slowly elevated to room temperature for a period of 16 hours. Water (30 ml), citric acid (1.61 g) and toluene (10 ml) were added to the reaction mixture for the distribution. The organic layer was washed with water (10 ml), water (10 ml), 6.7% aqueous sodium hydrogencarbonate solution (10 ml), 6.7% aqueous sodium hydrogencarbonate solution (10 ml), water (10 ml) and water (10 ml). After drying over sodium sulfate, the solvent was evaporated under reduced pressure to obtain the title compound in the form of a light yellow solid (5.13 g, 93%).

Workup

  1. waitthe temperature of the obtained mixture was slowly elevated to room temperature for a period of 16 hours
  2. washThe organic layer was washed with water (10 ml), water (10 ml), 6.7% aqueous sodium hydrogencarbonate solution (10 ml), 6.7% aqueous sodium hydrogencarbonate solution (10 ml), water (10 ml) and water (10 ml)
  3. dry with materialAfter drying over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bd74bdec61044b548ccdc0ec1c6611dd
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

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