Benzyl Alcohol → HCID 131715643, compound

HRID 1193541Notes

Reaction equation

HRID 1193541 reaction equation
[C:1]([C:8]([NH2:26])([CH2:12][CH2:13][CH2:14][C:15]1([CH:21]([C:23]([OH:25])=[O:24])C)[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].[CH2:27](O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CN([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40]N=1)C.[CH:44]1(N=C=NC2CCCCC2)CCCC[CH2:45]1>C(Cl)Cl>[C:1]([C:8]([NH2:26])([CH2:12][CH2:13][CH2:14][C:15]1([CH2:21][C:23]([O:25][CH2:38][C:43]2[CH:45]=[CH:44][CH:40]=[CH:41][CH:42]=2)=[O:24])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]([O:11][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:10])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 70377927HCID 70377927, 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 2.00-1.03 (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-a1adee894cc44dc48a8fe2e60e81da44
Source dataset
uspto-grants-1989_03
Patent number
US04810778

Reaction notes

Loading…