Dichloromethane → HCID 69284540, compound

HRID 2225229Notes

Reaction equation

HRID 2225229 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=[O:39])[CH2:16][NH:17][C:18](=[O:38])[C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=2[NH:29][C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:31])[C@H:10]([CH2:40][CH2:41][CH3:42])[CH2:9]1)(C)(C)C.ClCCl>C(O)(C(F)(F)F)=O>[NH2:7][C@@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([CH2:16][NH:17][C:18]([C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=2[NH:29][C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:31])=[O:38])=[O:39])[C@H:10]([CH2:40][CH2:41][CH3:42])[CH2:9]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 69286090HCID 69286090, compound

Product 1

HCID 69284540HCID 69284540, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Examples 2o and 2p, Step 4: A sample of (1R,3R,4S)-[4-(2-{2-[(morpholine-4-carbonyl)-amino]-5-trifluoromethyl-benzoylamino}-acetylamino)-3-propyl-cyclohexyl]-carbamic acid tert-butyl ester (200 mg) was dissolved in 1:2 TFA:dichloromethane and stirred for 30 min at RT before being concentrated in vacuo. The residue was redissolved in 1:2 TFA:dichloromethane and stirred for 30 min at RT before being concentrated in vacuo. The residue was dissolved in 1 N HCl and washed with Et2O; the aqueous phase was then basified (sat. NaHCO3 & a small amount of 1 N NaOH) and extracted (EtOAc, 2×). The organic extracts were combined, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford morpholine-4-carboxylic acid (2-{[(1S,2R,4R)-(4-amino-2-propyl-cyclohexylcarbamoyl)-methyl]-carbamoyl}-4-trifluoromethyl-phenyl)-amide as the free base (90 mg). MS found: (M+H)+=514.2.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. dissolutionThe residue was redissolved in 1:2 TFA
  3. concentrationbefore being concentrated in vacuo
  4. dissolutionThe residue was dissolved in 1 N HCl
  5. washwashed with Et2O
  6. extractiona small amount of 1 N NaOH) and extracted (EtOAc, 2×)
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71f9ab03d10a4b6f900712ff1a1ac0f9
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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