Hydrochloric Acid → 2-(7-chloro-4-(3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-3-yl)acetic acid

HRID 1054172Notes

Reaction equation

HRID 1054172 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([C:16]([C:18]3[CH:19]=[CH:20][C:21]4[O:26][CH2:25][C:24](=[O:27])[NH:23][C:22]=4[CH:28]=3)=[O:17])[CH:7]([CH2:10][C:11]([O:13]CC)=[O:12])[CH2:8][O:9][C:4]=2[CH:3]=1.[Li+].[OH-].Cl>C1COCC1>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([C:16]([C:18]3[CH:19]=[CH:20][C:21]4[O:26][CH2:25][C:24](=[O:27])[NH:23][C:22]=4[CH:28]=3)=[O:17])[CH:7]([CH2:10][C:11]([OH:13])=[O:12])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 131736328Ethyl {7-chloro-4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetate2×

Product 1

HCID 1185996432-(7-chloro-4-(3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-3-yl)acetic acidYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl {7-chloro-4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetate (Intermediate 21, 42 mg, 0.10 mmol) and LiOH (1 M, 0.146 mL, 0.15 mmol) in THF (2 mL) was stirred at rt for 2 h. Additional LiOH (1 M, 0.070 mL, 0.07 mmol) was added and the mixture was stirred for 2 h. HCl (1 M, 5 mL) was added and the aq. phase was extracted with DCM (3×5 mL). The combined organic layers were dried by passage through a phase separator and concentrated in vacuo providing the title compound (38.0 mg, 97%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 2 h
  2. extractionthe aq. phase was extracted with DCM (3×5 mL)
  3. customThe combined organic layers were dried by passage through a phase separator
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-427cf1aac3a542e8882fce3d7003175c
Source dataset
uspto-grants-2016_07
Patent number
US09394291B2

Reaction notes

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