Dichloromethane → HCID 66662788, compound

HRID 969231Notes

Reaction equation

HRID 969231 reaction equation
[CH3:1][C:2]1([CH3:37])[C:6]2([CH2:10][CH2:9][N:8]([C:11]([C:13]3([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31](C)(C)C)=[O:29])[CH2:24][CH2:23]5)=[CH:18][C:17]=4[F:35])[CH2:15][CH2:14]3)=[O:12])[CH2:7]2)[O:5][C:4](=[O:36])[CH2:3]1.C(O)(C(F)(F)F)=O.C(Cl)Cl.C(N(CC)CC)C.ClC(OC)=O>>[CH3:1][C:2]1([CH3:37])[C:6]2([CH2:10][CH2:9][N:8]([C:11]([C:13]3([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][N:25]([C:28]([O:30][CH3:31])=[O:29])[CH2:24][CH2:23]5)=[CH:18][C:17]=4[F:35])[CH2:15][CH2:14]3)=[O:12])[CH2:7]2)[O:5][C:4](=[O:36])[CH2:3]1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acid2×HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 66661985HCID 66661985, compound

Product 1

HCID 66662788HCID 66662788, compound

Procedure

tert-Butyl 4-(4-{1-[(4,4-dimethyl-2-oxo-1-oxa-7-azaspiro[4.4]non-7-yl)carbonyl]cyclopropyl}-3-fluorophenyl)piperazine-1-carboxylate (25.0 mg, 0.0000485 mol) was treated with TFA. After stirring at rt for 30 min, the volatiles were removed in-vacuo and the residue was dried on high vaccum. The resultant TFA salt was dissolved in methylene chloride (0.25 mL, 0.0039 mol) and to this was added triethylamine (0.0203 mL, 0.000145 mol) followed by methyl chloroformate (0.00749 mL, 0.0000970 mol). The reaction mixture was stirred at rt for 1 h and then the volatiles were removed in-vacuo. The residue was diluted with methanol and applied directly on RP-HPLC to yield the desired product. LCMS (M+H) 474.2.

Workup

  1. customthe volatiles were removed in-vacuo
  2. customthe residue was dried on high vaccum
  3. stirringThe reaction mixture was stirred at rt for 1 h
  4. customthe volatiles were removed in-vacuo
  5. additionThe residue was diluted with methanol

Sources & evidence

ORD record
ord-043e6785235a4953b9b5ae8dc7b4c106
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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