Hydrochloric Acid → HCID 66736794, compound

HRID 1640539Notes

Reaction equation

HRID 1640539 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[NH:10][C:11]1[CH:12]=[CH:13][C:14]2[O:19][CH2:18][C:17](=[O:20])[NH:16][C:15]=2[CH:21]=1)[C:2]1C=CC=CC=1.[C:23]([O:27][Li])([CH3:26])([CH3:25])[CH3:24].C1COCC1.Cl.[CH3:35][N:36]([CH:38]=[O:39])C>>[C:23]([O:27][C:38](=[O:39])[NH:36][CH2:35][C@H:1]1[O:8][C:9](=[O:22])[N:10]([C:11]2[CH:12]=[CH:13][C:14]3[O:19][CH2:18][C:17](=[O:20])[NH:16][C:15]=3[CH:21]=2)[CH2:2]1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 66737621HCID 66737621, compoundHCID 178506942HCID 178506942, compound

Product 1

HCID 66736794HCID 66736794, compoundYield 29%

Conditions

Temperature
0 °C

Procedure

A solution of (3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-carbamic acid benzyl ester (prepared according to method C, 1.4 g, 4.7 mmol) and intermediate 4.i (0.984 g, 4.7 mmol) in DMF (15 mL) at 0° C. was treated dropwise with a 2.2M solution of t-BuOLi in THF (6.4 mL, 3 eq.). The mixture was stirred at 0° C. for 1 h and at rt overnight. 1M HCl (9.4 mL) was added and the mixture partitioned between EA and water. The aq. phase was extracted once more with EA and the combined org. phases were washed several times with water and brine, dried over MgSO4 and concentrated. The residue was purified by FC (Hept/EA 1:2, EA) to give the title intermediate as a colourless solid (0.5 g, 29% yield).

Workup

  1. customthe mixture partitioned between EA and water
  2. extractionThe aq. phase was extracted once more with EA
  3. washphases were washed several times with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by FC (Hept/EA 1:2, EA)

Sources & evidence

ORD record
ord-0e76bfc29e3d4c3fad6161521e52af4b
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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