Benzyl Alcohol → BOC-L-Alanine benzyl ester

HRID 658140Notes

Reaction equation

HRID 658140 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 10972741BOC-L-Alanine benzyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N2-(tert-Butoxycarbonyl)-L-alanine (1.13 g, 5.83 mmol) is dissolved in dry DCM (6 ml), some 3 Å molecular sieves are added, and the mixture is then cooled to 0° C. Benzyl alcohol (1.81 ml, 17.48 mmol, 3 equivalents), EDCI (2.23 g, 11.65 mmol, 2 equivalents), and DMAP (71 mg, 0.58 mmol, 0.1 equivalent) are added. The mixture is stirred for 150 min, during which it is allowed to slowly warm to RT. The mixture is then concentrated to dryness and the residue is worked up by chromatography (Biotage, cyclohexane-ethyl acetate 9:1). Product-containing fractions are combined and concentrated. The title compound is obtained in a yield of 1.03 g (63% of theory).

Workup

  1. additionsome 3 Å molecular sieves are added
  2. temperatureto slowly warm to RT
  3. concentrationThe mixture is then concentrated to dryness
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4bb3046da8214611b31a702bd301d7c5
Source dataset
uspto-grants-2011_12
Patent number
US08076285B2

Reaction notes

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