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Acetic Acid → HCID 11291125, compound

HRID 459916
Notes
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Reaction equation

HRID 459916 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[C:18]1([CH2:24][CH2:25][CH2:26][NH2:27])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C(O)(=O)C>C(Cl)Cl>[C:18]1([CH2:24][CH2:25][CH2:26][NH:27][CH:2]2[CH2:7][CH2:6][CH:5]([O:8][C:9]3[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=3)[CH2:4][CH2:3]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 162593-PhenylpropylamineHCID 2724942TriacetoxyborohydrideHCID 18445301HCID 18445301, compound

Product 1

HCID 11291125HCID 11291125, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Combine 4-(4-oxo-cyclohexyloxy)-benzamide (20 mg, 0.085 mmol), 3-phenyl-propylamine (11 mg, 0.085 mmol), triacetoxyborohydride (23 mg, 0.111 mmol) and acetic acid (5 μL, 0.085 mmol) in CH2Cl2 (1 mL). Let stir overnight. Purify by SCX column (ammonia in methanol 2.0M). Triturate the residue with EtOAc/hexanes 1/1 to provide a white powder (25 mg, 86%).

Workup

  1. customPurify by SCX column (ammonia in methanol 2.0M)
  2. customTriturate the residue with EtOAc/hexanes 1/1

Sources & evidence

ORD record
ord-30ff7548533a413cb2f3d05e86970c8a
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07196100B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes