Benzyl Alcohol → HCID 131715643, compound

HRID 1165355Notes

Reaction equation

HRID 1165355 reaction equation
[C:1]([C:8]([NH2:25])([CH2:12][CH2:13][CH2:14][C:15]1([CH2:21][C:22]([OH:24])=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]([OH:11])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:26](O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CN([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39]N=1)C.[CH:43]1(N=C=NC2CCCCC2)CCCC[CH2:44]1>C(Cl)Cl>[C:1]([C:8]([NH2:25])([CH2:12][CH2:13][CH2:14][C:15]1([CH2:21][C:22]([O:24][CH2:37][C:42]2[CH:44]=[CH:43][CH:39]=[CH:40][CH:41]=2)=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[C:9]([O:11][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:10])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 70360340HCID 70360340, compound

Product 1

HCID 131715643HCID 131715643, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boc-diacid (F) (1.34 g, 3.75 mmol) in methylene chloride (30 ml) was treated with benzyl alcohol (1.94 ml, 18.75 mmol), dimethylaminopyridine (1.01 g, 8.25 mmol) and N,N'-dicyclohexylcarbodiimide (1.70 g, 8.25 mmol) at room temperature and the mixture was stirred at room temperature for 72 hours. The reaction mixture was then filtered, evaporated at reduced pressure and the residue was dissolved in ethyl acetate which was washed with 3N hydrochloric acid, dried over MgSO4 and evaporated at reduced pressure. Purification of the residue by flash chromatography (silica gel, 15% ethyl acetate/hexane) gave 1.27 g (63%) of (I): 1HNMR (CDCl3): 7.35 (S, 10H), 5.15 (d,J=2.4 Hz, 2H), 5.07 (S, 2H) 5.05-4.70 (m, 1H), 4.50-4.05 (m, 1H), 2.27 (S, 2H), 1.45 (S, 9H) and 2.00-03 (m, 16H).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customevaporated at reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate which
  4. washwas washed with 3N hydrochloric acid
  5. dry with materialdried over MgSO4
  6. customevaporated at reduced pressure
  7. customPurification of the residue by flash chromatography (silica gel, 15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-28160d12ec4a4ecc9a6bfdbeb78fd17d
Source dataset
uspto-grants-1990_03
Patent number
US04908475

Reaction notes

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