Dicyclohexylcarbodiimide → HCID 70486596, compound

HRID 484751Notes

Reaction equation

HRID 484751 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([O:20][C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([OH:27])=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].[CH2:31]([S:33]([NH2:36])(=[O:35])=[O:34])[CH3:32]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:31]([S:33]([NH2:36])(=[O:35])=[O:34])[CH3:32].[C:16]([O:20][C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([OH:27])=[O:26])=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 73702EthanesulfonamideHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Product 1

HCID 70486596HCID 70486596, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of dicyclohexylcarbodiimide (103 g.) in methylene chloride (250 ml.) was added to a stirred solution of N-t-butoxycarbonyl-L-proline (101 g.), ethanesulphonamide (54.5 g.) and 4-dimethylaminopyridine (61 g.) in methylene chloride (2500 ml.) which was cooled to 0° C., and the mixture was allowed to warm up to laboratory temperature, stirred at that temperature for 4 days and then filtered. The filtrate was evaporated to dryness and the residue was partitioned between diethyl ether (1000 ml.) and saturated sodium bicarbonate solution (1000 ml.). The aqueous solution was separated, neutralised with concentrated aqueous hydrochloric acid, acidified with citric acid and extracted with ethyl acetate. The extract was dried and evaporated to dryness, the residue was stirred with diethyl ether and the mixture was filtered. There was thus obtained as solid product N-t-butoxycarbonyl-L-proline ethanesulphonamide, m.p. 170°-172° C.

Workup

  1. temperatureto warm up to laboratory temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was partitioned between diethyl ether (1000 ml.) and saturated sodium bicarbonate solution (1000 ml.)
  5. customThe aqueous solution was separated
  6. extractionextracted with ethyl acetate
  7. customThe extract was dried
  8. customevaporated to dryness
  9. stirringthe residue was stirred with diethyl ether
  10. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-b3c8f92514e447d086a5403244e37395
Source dataset
uspto-grants-1985_08
Patent number
US04533656

Reaction notes

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