Sodium Carbonate → 61350-60-5

HRID 1186019Notes

Reaction equation

HRID 1186019 reaction equation
C(O[C@H](C)[C@H](NC(C1(CC2C=CC=CC=2)CCCN1)=O)C(OC)=O)(=O)C.C([O-])([O-])=O.[Na+].[Na+].[CH2:33]([O:40][C:41]([N:43]1[CH2:47][CH2:46][CH2:45][C@H:44]1[C:48]([OH:50])=O)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O=S(Cl)[Cl:53]>C(Cl)Cl.O>[Cl:53][C:48]([C@@H:44]1[CH2:45][CH2:46][CH2:47][N:43]1[C:41]([O:40][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:42])=[O:50]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 101987Benzyloxycarbonyl-L-prolineHCID 71245465HCID 71245465, compound

Product 1

HCID 1103285461350-60-5

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of compound 6 (1 g, 2.76 mmol) and Na2CO3 (732 mg, 6.90 mmol) in CH2Cl2:H2O (20 mL, 1:1) was added a solution of acid chloride [To a solution of (S)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid (825 mg, 3.31 mmol) in CH2Cl2 (20 mL) was added SOCl2 (0.60 mL) drop wise at 0° C. and was refluxed for 2 h. The volatiles were removed under reduced pressure to yield (S)-benzyl 2-(chlorocarbonyl)pyrrolidine-1-carboxylate] in CH2Cl2 and the reaction mixture was stirred at RT for 2 h. The volatiles were evaporated under reduced pressure. The residue was diluted with CH2Cl2 (100 mL), filtered and the filtrate was concentrated under vacuum. The crude residue was purified by column chromatography using 60% EtOAc/Hexane as eluent to afford compound 7 (750 mg, 45%).

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-32a68b0f1f454106b8768d0247554275
Source dataset
uspto-grants-2014_03
Patent number
US08673843B2

Reaction notes

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