Dicyclohexylcarbodiimide → HCID 54546036, compound

HRID 1735509Notes

Reaction equation

HRID 1735509 reaction equation
O.O.[CH2:3]([O:10][C:11]([NH:13][C@H:14]([C:23]([OH:25])=O)[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:26]1[CH2:31][CH2:30][CH:29]([O:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:28][CH2:27]1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.ON1C(=O)CCC1=O>[CH2:3]([O:10][C:11]([NH:13][C@H:14]([C:23]([N:26]1[CH2:27][CH2:28][CH:29]([O:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:31]1)=[O:25])[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 10036224Tert-butyl (piperidin-4-yloxy)-acetateHCID 67573103HCID 67573103, compound

Product 1

HCID 54546036HCID 54546036, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 80170N-HydroxysuccinimideCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

10.2 g (30 mmol) of N-(benzyloxycarbonyl)-L-tyrosine dihydrate, 6.48 g (30 mmol) of t-butyl (4-piperidinyloxy)acetate and 0.17 g (1.5 mmol) of N-hydroxysuccinimide were dissolved in 200 ml of ethyl acetate while stirring under argon. 6.5 g (31.5 mmol) of dicyclohexylcarbodiimide dissolved in 33 ml of ethyl acetate were added dropwise to the yellowish solution within 19 minutes. A suspension formed slowly and this was stirred at 22° for 22 hours. The precipitated dicyclohexylurea was filtered off and the filtrate was extracted with 1N hydrochloric acid, water and sodium chloride solution. The organic phase was dried over sodium sulphate and, after removing the drying agent, evaporated. 13.1 g of t-butyl [[1-[N-[(benzyloxy)carbonyl]-L-tyrosyl]-4-piperidinyl]oxy]acetate were obtained as a white, hard foam, the microanalysis of which corresponded to that of authentic material.

Workup

  1. additionwere added dropwise to the yellowish solution within 19 minutes
  2. customA suspension formed slowly
  3. stirringthis was stirred at 22° for 22 hours
  4. filtrationThe precipitated dicyclohexylurea was filtered off
  5. extractionthe filtrate was extracted with 1N hydrochloric acid, water and sodium chloride solution
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. customafter removing the drying agent
  8. customevaporated

Sources & evidence

ORD record
ord-c66b87c9870c4b34a510a2d48b5dc483
Source dataset
uspto-grants-1996_07
Patent number
US05536816

Reaction notes

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