Ammonia → HCID 10149461, compound

HRID 896147Notes

Reaction equation

HRID 896147 reaction equation
C[O:2][C:3]([C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:22]=[CH:21][C:14]3[N:15]([CH3:20])[C:16](=[O:19])[CH2:17][O:18][C:13]=3[CH:12]=2)[CH2:6]1)=O.[NH3:23]>CO.CCOCC>[CH3:20][N:15]1[C:14]2[CH:21]=[CH:22][C:11]([N:7]3[CH2:6][C@H:5]([C:3]([NH2:23])=[O:2])[O:9][C:8]3=[O:10])=[CH:12][C:13]=2[O:18][CH2:17][C:16]1=[O:19]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 68485955HCID 68485955, compound

Product 1

HCID 10149461HCID 10149461, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of (5R)-3-(3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazin-7-yl)-2-oxo-oxazolidine-5-carboxylic acid methyl ester (Step 2, 2.41 g, 7.87 mmol) in MeOH (25 mL) is added 2M NH3 in MeOH (25 mL, 50 mmol). The resulting clear solution becomes turbid after ˜10 min. This mixture is stirred for 16 h at which time the reaction is diluted with ether (20 mL) and the resulting white solid filtered off. This white solid is washed with several portion of ether (50 mL) and dried under high vacuum to give the title compound (1.87 g, 81%), 1H NMR (300 MHz, DMSO) δ 7.85 (br s, 1H), 7.60 (br s, 1H), 7.31-7.14 (m, 3H), 5.00 (dd, 1H), 4.65 (s, 2H), 4.21 (t, 1H), 3.97 (dd, 1H), 3.32 (s, 3H); MS for C14H13N3O5 m/z 292.5 (M+H)+.

Workup

  1. customafter ˜10 min
  2. filtrationthe resulting white solid filtered off
  3. washThis white solid is washed with several portion of ether (50 mL)
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-6ee309e93f194cba9d5a9d3692b6f3dc
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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