Diisopropylcarbodiimide → HCID 131725937, compound

HRID 902928Notes

Reaction equation

HRID 902928 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][CH:8]([C:14]([O:16][CH3:17])=[O:15])[CH2:9][CH2:10][C:11]([OH:13])=O)([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.[C:29]([O:48][NH2:49])([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CC(C)N=C=NC(C)C>CN(C=O)C>[CH3:17][O:16][C:14](=[O:15])[CH:8]([CH2:9][CH2:10][C:11](=[O:13])[NH:49][O:48][C:29]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:18]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3015602O-(triphenylmethyl)hydroxylamineHCID 865943843-Methoxycarbonyl-hexanedioic acid 1-tert-butyl ester

Product 1

HCID 131725937HCID 131725937, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound of example 64 (1.10 g, 4.19 mmol) and HOBt (0.70 g, 5.03 mmol) in DMF (5 mL) were added O-trityl hydroxylamine (1.82 g, 6.28 mmol) and DIC (800 μL), respectively. The reaction mixture was stirred for 24 h at room temperature. The reaction mixture was partitioned between HCl (1N, excess) and ethyl acetate. The aqueous phase was extracted several times with ethyl acetate. The recombined organic layer was washed with brine, saturated sodium bicarbonate, and brine. The solvent was evaporated following drying over sodium sulfate, and the crude was flashed with 20-30% ethyl acetate in hexanes. 1H-NMR(CDCl3, 400 MHz: 1.42(s, 9H); 1.58, 2.14, 2.47(3m, 7H); 3.69(s, 3H); 7.34(m, 15H); 7.88(d, broad, 1H).

Workup

  1. customThe reaction mixture was partitioned between HCl (1N, excess) and ethyl acetate
  2. extractionThe aqueous phase was extracted several times with ethyl acetate
  3. washThe recombined organic layer was washed with brine, saturated sodium bicarbonate, and brine
  4. customThe solvent was evaporated
  5. dry with materialfollowing drying over sodium sulfate

Sources & evidence

ORD record
ord-60faa6ff9834475b8f40274a128cb2d3
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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