Methylamine → HCID 68902881, compound

HRID 2110335Notes

Reaction equation

[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([CH:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]([OH:18])[C:13](OCC)=[O:14])[CH2:3][CH2:2]1.[CH3:25][NH2:26]>>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([CH:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]([OH:18])[C:13]([NH:26][CH3:25])=[O:14])[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 6329Methylamine

HCID 86600862HCID 86600862, compound

Product 1

HCID 68902881HCID 68902881, compoundYield 87%

Conditions

Temperature: 70 °C

Procedure

A mixture of ethyl (2RS,3RS)-3-(2,3-dihydro-4H-1,4-benzoxazin-4-yl)-2-hydroxy-3-phenylpropanoate (283 mg, 0.864 mmol) and ethanolic methylamine solution (5 mL, 33% in ethanol) was stirred at 70° C. in a sealed tube for 5 hours. After cooling, all volatiles were removed under reduced pressure. The resulting yellow solid was purified via Biotage Horizon (FLASH 12 S, silica, 20%, 35%, 50% EtOAc/hexane) to yield 235 mg (87%) (2RS,3RS)-3-(2,3-dihydro-4H-1,4-benzoxazin-4-yl)-2-hydroxy-N-methyl-3 phenylpropanamide as a white solid. MS (ESI) m/z 311.0 ([M−H]−).

Workup

temperatureAfter cooling
customall volatiles were removed under reduced pressure
customThe resulting yellow solid was purified via Biotage Horizon (FLASH 12 S, silica, 20%, 35%, 50% EtOAc/hexane)

Sources & evidence

ORD record: ord-726d85a200ba4c818b043020108f5714
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517899B2

Reaction notes

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