HCID 68633648, compound → HCID 68634512, compound

HRID 2403509Notes

Reaction equation

HRID 2403509 reaction equation
C([O:8][C:9]1[C:10]([O:25][CH3:26])=[CH:11][C:12]2[C:18](=[O:19])[N:17]3[CH2:20][CH2:21][CH2:22][CH2:23][C@@H:16]3[CH:15]=[N:14][C:13]=2[CH:24]=1)C1C=CC=CC=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[OH:8][C:9]1[C:10]([O:25][CH3:26])=[CH:11][C:12]2[C:18](=[O:19])[N:17]3[CH2:20][CH2:21][CH2:22][CH2:23][C@@H:16]3[CH:15]=[N:14][C:13]=2[CH:24]=1

Participants

4

Reactant 1

HCID 68633648HCID 68633648, compound

Product 1

HCID 68634512HCID 68634512, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To (R,Z)-3-(benzyloxy)-2-methoxy-7,8,9,10-tetrahydrobenzo[e]pyrido[1,2-a][1,4]diazepin-12(6aH)-one (241) (215 mg, 0.614 mmol) in 25 ml of CH2Cl2 at 0° C. was added 25 ml of CH2SO3H. The mixture was stirred at 0° C. for 10 min and then at RT for 2 h, diluted with CH2Cl2, neutralized with cold 1.0 M NaHCO3, extracted with CH2Cl2, dried over Na2SO4, filtered, evaporated and purified on SiO2 chromatography eluted with CH3OH/CH2Cl2 (1:15) to afford 122 mg (70%) of the title product. 1H NMR (CDCl3), 7.75 (d, 1H, J=5.7 Hz), 7.28 (s, 1H), 6.70 (s, 1H), 4.08 (m, 1H), 3.83 (d, 3H), 3.61 (m, 1H), 3.08 (m, 1H), 1.91 (m, 1H), 1.81 (m, 1H), 1.71˜1.55 (m, 4H); 13C NMR 167.81, 163.46, 148.53, 145.71, 140.84, 121.23, 111.89, 111.39, 56.45, 49.83, 39.96, 24.71, 23.22, 18.60; MS m/z+283.7 (M+Na).

Workup

  1. waitat RT for 2 h
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. custompurified on SiO2 chromatography
  7. washeluted with CH3OH/CH2Cl2 (1:15)

Sources & evidence

ORD record
ord-d3c5b308782b4af3bdd47607c50435b1
Source dataset
uspto-grants-2014_08
Patent number
US08802667B2

Reaction notes

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