Acetic Acid → HCID 86586725, compound

HRID 2088184Notes

Reaction equation

HRID 2088184 reaction equation
[NH2:1][C@@H:2]1[CH2:8][C@:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C@H:3]1[CH2:4][CH2:5][C@H:6]2[O:23][CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=1.[C:39](O)(=[O:41])[CH3:40].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[C:39]([NH:1][C@@H:2]1[CH2:8][C@:7]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C@H:3]1[CH2:4][CH2:5][C@H:6]2[O:23][CH2:24][C:25]1[CH:26]=[C:27]([C:35]([F:38])([F:36])[F:37])[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=1)(=[O:41])[CH3:40]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86586726HCID 86586726, compound

Product 1

HCID 86586725HCID 86586725, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(1R*,2R*,5S*,6R*)-6-Amino-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane (Example 108; 475 mg, 0.89 mmol), glacial acetic acid (0.076 ml, 1.34 mmol), triethylamine (0.14 ml, 0.98 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (257 mg, 1.34 mmol) and 4-dimethylaminopyridine (2 crystals) were combined in dichloromethane (4 ml) and stirred overnight at room temperature. The reaction mixture was washed with water and extracted with dichloromethane (×3). The organics were dried (MgSO4), and concentrated in vacuo to give the title compound as a yellow oil (384 mg, 75%).

Workup

  1. washThe reaction mixture was washed with water
  2. extractionextracted with dichloromethane (×3)
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-342a2edc736c494d85ba5df603d14b94
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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