Hydrochloric Acid → HCID 118036715, compound

HRID 1777982Notes

Reaction equation

HRID 1777982 reaction equation
[H-].[Na+].Br[CH2:4][C:5]([OH:7])=[O:6].[C:8]([NH:15][C@@H:16]([CH2:18][OH:19])[CH3:17])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Cl>C1COCC1.O.CCOC(C)=O>[C:11]([O:10][C:8]([NH:15][C@H:16]([CH3:17])[CH2:18][O:19][CH2:4][C:5]([OH:7])=[O:6])=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate

Product 1

HCID 118036715HCID 118036715, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% w/w dispersion in mineral oil, 4.58 g, 114 mmol) was added portionwise to a solution of 2-bromoacetic acid (5.3 g, 38.1 mmol) and N-Boc-D-alaninol (10.0 g, 57.2 mmol) in THF (100 ml) at 0° C. The reaction mixture was stirred for 48 h at room temperature, diluted with water, washed 2× with EtOAc, hydrochloric acid (1M, 84 ml, 84 mmol) was added to the aqueous layer (pH 2-3) and the aqueous layer extracted 2× with DCM. The DCM layers were dried over Na2SO4 and evaporated to give the title compound as a yellow oil which crystallised on standing. (MS) ESI-MS 256.2 [M−H]−.

Workup

  1. extractionthe aqueous layer extracted 2× with DCM
  2. dry with materialThe DCM layers were dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-24a6ad36468f4d67bf19e2f0d79f5876
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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