1-Hydroxybenzotriazole → HCID 117690875, compound

HRID 58915Notes

Reaction equation

HRID 58915 reaction equation
Cl.[NH2:2][C@@H:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5].[O:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16](O)=[O:17])[CH2:11][CH2:10]1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[O:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]([NH:2][C@@H:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5])=[O:17])[CH2:11][CH2:10]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4389684-Morpholineacetic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2733257Alanine methyl ester hydrochloride

Product 1

HCID 117690875HCID 117690875, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (S)-methyl 2-aminopropanoate HCl salt (5.0 g, 35.8 mmol) in DMF (30 mL) at 0° C. was added morpholinoacetic acid (5.19 g, 35.8 mmol), HOBt (7.74 g, 57.3 mmol), HBTU (21.7 g, 57.3 mmol), followed by DIEA (24.9 mL, 0.143 mol). The mixture was allowed to stir for 15 min at which time it was quenched with sodium bicarbonate (sat.), extracted with ethyl acetate (2×), dried with sodium sulfate, filtered, and concentrated to provide (S)-methyl 2-(2-morpholinoacetamido)propanoate (quant. yield) as a colorless solid.

Workup

  1. customwas quenched with sodium bicarbonate (sat.)
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d07c83d20218440f89ffa01aacc3008c
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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