Benzyl Alcohol → HCID 11810403, compound

HRID 2399236Notes

Reaction equation

HRID 2399236 reaction equation
CN(CCCN=C=NCC)C.[NH:12]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:13]([C:21]([OH:23])=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:31](O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.N1(C2C=CN=CC=2)CCCC1>ClCCl>[NH:12]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:13]([C:21]([O:23][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 755674-PyrrolidinopyridineHCID 637610Boc-D-phenylalanine

Product 1

HCID 11810403HCID 11810403, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethylaminopropylethylcarbodiimide (EDC) (1.68 E, 8.78mmol) was added to a solution of the crude N-Boc-D-Phe (as described previously, assumed to be 7.32 mmol), benzyl alcohol (1.14 ml, 11.0 mmol) and 4-pyrrollidinopyridine (217 mg, 1.46 mmol) in dichloromethane (73.2 ml). The reaction mixture was stirred at room temperature overnight, diluted with dichloromethane, and washed sequentially with a dilute solution of HCl (<5%, pH 3.0), a solution of saturated sodium bicarbonate, and brine. The combined organic layers were dried over MgSO4 and concentrated to obtain a yellow oil. This substance was subjected to silica gel chromatography, eluted with a solution that was 5:1 hexanes:ethyl acetate, and resulted in a yield of 2.31 g of N-Boc-D-Phe-OBn.

Workup

  1. washwashed sequentially with a dilute solution of HCl (<5%, pH 3.0)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated
  4. customto obtain a yellow oil
  5. washeluted with a solution that

Sources & evidence

ORD record
ord-8c9433b98b914f50a73e92d2b3529266
Source dataset
uspto-grants-1995_09
Patent number
US05447915

Reaction notes

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