Diisopropylethylamine → HCID 44583623, compound

HRID 473790Notes

Reaction equation

HRID 473790 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:13]([C@H:15]3[CH2:22][CH2:21][C:18]4([CH2:20][CH2:19]4)[CH2:17][C@@H:16]3[C:23]([OH:25])=O)=[O:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.NO.F[P-](F)(F)(F)(F)F.[N:36]1([O:45][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[OH:45][NH:36][C:23]([C@@H:16]1[C@@H:15]([C:13]([N:10]2[CH2:9][CH2:8][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11]2)=[O:14])[CH2:22][CH2:21][C:18]2([CH2:19][CH2:20]2)[CH2:17]1)=[O:25]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 443297Hydroxyamine hydrochlorideHCID 67006766HCID 67006766, compound

Product 1

HCID 44583623HCID 44583623, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from step 9 (36 mg, 0.105 mmole), and hydroxylamine hydrochloride (22 mg, 0.315 mmole) were dissolved in DMF (0.70 ml). To the solution, BOP (49 mg, 0.11 mmole) was added with stirring at r.t. for 10 min. DIEA (61 mg, 0.47 mmole) was added. The mixture was stirred at r.t. for 2 hours. The product was purified with preparative HPLC providing 22 mg of (5S,6S)—N-hydroxy-6-((4-phenylpiperazin-1-yl)carbonyl)spiro(2.5) octane-5-carboxamide. Yield: 44%. MS: M/Z 358.2 (M+H)+; 380.2 (M+Na)+; 737.2 (2M+Na)+.

Workup

  1. stirringThe mixture was stirred at r.t. for 2 hours
  2. customThe product was purified with preparative HPLC

Sources & evidence

ORD record
ord-55df98088e684882bff96b746910e75d
Source dataset
uspto-grants-2014_01
Patent number
US08637497B2

Reaction notes

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