Tetrahydrofuran → Carbamate

HRID 18046

Reaction equation

HRID 18046 reaction equation
[C:1]([O:5][C:6](=[O:17])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:18](=[O:21])(O)[O-:19].[Na+].C1COCC1.Cl[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>C(OCC)C.O>[C:1]([O:5][C:6](=[O:17])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[NH:8][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])([CH3:4])([CH3:2])[CH3:3].[C:18](=[O:21])([O-:19])[NH2:8]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 6950582L-Tyrosine 1,1-dimethylethyl ester

Product 2

HCID 276CarbamateHCID 11428694Z-Tyr-OtBu

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. suspension of L-tyrosine tert-butyl ester (Bachem, 1.0. eq) and sodium bicarbonate (2.0 eq) in a 1:1 mixture of THF and water was added slowly with stirring benzyl chloroformate (1. 1 eq). After the addition, the mixture was stirred at 0° C. for 3 h and at room temperature for 24 h. The mixture was diluted with diethyl ether, and the aqueous layer was separated. The organic extracts were washed with saturated sodium chloride, treated with anhydrous magnesium sulfate, filtered, and evaporated to afford N-benzyloxycarbonyl-L-tyrosine tert-butyl ester of sufficient purity for immediate conversion of the tyrosine hydroxyl into a carbamate.

Workup

  1. additionAfter the addition
  2. customthe aqueous layer was separated
  3. washThe organic extracts were washed with saturated sodium chloride
  4. additiontreated with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4a6c1f1dc3e74d41b45ee6e37120b17a
Source dataset
uspto-grants-2010_06
Patent number
US07741328B2

Linked notes

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