tert-Butyl carbamate → [1-(Benzooxazol-2-yl-hydroxy-methyl)-propyl]-carbamic acid tert-butyl ester

HRID 1830160Notes

Reaction equation

HRID 1830160 reaction equation
CCN(C(C)C)C(C)C.[NH2:10][CH:11]([CH2:23][CH3:24])[CH:12]([C:14]1[O:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1)[OH:13].[C:25]([O:29][C:30](=[O:32])N)([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[C:25]([O:29][C:30](=[O:32])[NH:10][CH:11]([CH:12]([C:14]1[O:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1)[OH:13])[CH2:23][CH3:24])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 77922tert-Butyl carbamateHCID 81531DiisopropylethylamineHCID 219626762-Amino-1-benzooxazol-2-yl-butan-1-ol

Product 1

HCID 21031071[1-(Benzooxazol-2-yl-hydroxy-methyl)-propyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (0.35 ml, 2 mmol) and di-tret-butyl dicarbonate (355 mg, 1.63 mmol) were added to a solution of 2-Amino-1-benzooxazol-2-yl-butan-1-ol (320 mg, 1.55 mmol) in dry methylene chloride (10 ml) and stirred at room temperature for 4 hrs. The reaction was quenched with saturated aqueous NH4Cl and the pH was adjusted to neutral. Oraganic layer separated and the aqueous layer extracted with methylene chloride. The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure to give, 1-(Benzooxazol-2-yl-hydroxy-methyl)-propyl]-carbamic acid tert-butyl ester (500 mg).

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. customOraganic layer separated
  3. extractionthe aqueous layer extracted with methylene chloride
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give

Sources & evidence

ORD record
ord-762e48b7a0ae46418962c3827eadfa8a
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

Loading…