1,2-Dichloroethane → (R)-tert-butyl 1-amino-3-methoxy-1-oxopropan-2-ylcarbamate

HRID 84850Notes

Reaction equation

HRID 84850 reaction equation
[C:1]([NH:8][C@@H:9]([C:13]([OH:15])=O)[CH2:10][O:11][CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=C2[N:22]=NN(O)C2=CC=1.O.C(Cl)CCl.[NH4+].[OH-]>CN(C=O)C.CCOC(C)=O.O>[NH2:22][C:13](=[O:15])[C@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH2:10][O:11][CH3:12]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 27960291-Hydroxybenzotriazole hydrateHCID 27281801(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxypropanoic acid

Product 1

HCID 86666155(R)-tert-butyl 1-amino-3-methoxy-1-oxopropan-2-ylcarbamateYield 22.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-Boc-O-methyl-D-serine (438 mg, 2.00 mmol), HOBt monohydrate (364 mg, 2.38 mmol) and EDC (460 mg, 2.39 mmol) in DMF (9 mL) was stirred at room temperature for 2 h, conc. NH4OH (0.700 mL, ca. 9.80 mmol) was added. The mixture was stirred for 18 h. Water and EtOAc were added. The organic phase was washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-tert-butyl 1-amino-3-methoxy-1-oxopropan-2-ylcarbamate (100 mg). The aqueous phase was further extracted with nBuOH (30 mL). The nBuOH solution was washed with 5% NaHCO3, then was concentrated in vacuo to give another portion of (R)-tert-butyl 1-amino-3-methoxy-1-oxopropan-2-ylcarbamate (242 mg).

Workup

  1. washThe organic phase was washed with 5% NaHCO3
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96fee265ed4d4733a623203da84abf81
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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