N-(tert-butoxycarbonyl)glycine → tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

HRID 2091505Notes

Reaction equation

HRID 2091505 reaction equation
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=O.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[CH3:50][NH:51][O:52][CH3:53]>C(Cl)Cl>[CH3:53][O:52][N:51]([CH3:50])[C:3](=[O:5])[CH2:2][NH:1][C:6](=[O:7])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531Diisopropylethylamine2×HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamateYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of Boc-Gly-OH (20 g, 114.1 mmol), DIPEA (19.8 mL, 114.1 mmol) and BOP (50.5 g, 114.1 mmol) in DCM (20 mL) was added a pre-mixed solution of N,O-dimethylhydroxylamine hydrochloride (11.2 g, 114.1 mmol) and DIPEA (19.8 mL, 114.1 mmol) in DCM (20 mL) at room temperature. The resulting mixture was stirred for 16 h then washed with 1N HCl (3×120 mL), H2O (3×120 mL), saturated NaHCO3 aqueous solution (3×120 mL) and brine (40 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give 27 as a white solid (20 g, 80%), which was used in the next step without further purification.

Workup

  1. washthen washed with 1N HCl (3×120 mL), H2O (3×120 mL), saturated NaHCO3 aqueous solution (3×120 mL) and brine (40 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfbdeeae3305427b89dadb2cfd50d9d5
Source dataset
uspto-grants-2013_05
Patent number
US08440653B2

Reaction notes

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