Diisopropylcarbodiimide → HCID 69211444, compound

HRID 902940Notes

Reaction equation

HRID 902940 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][CH:8]([CH2:12][CH2:13][CH2:14][S:15][C:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.[C:46]1([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:51]=[CH:50][C:49]([CH2:52][CH2:53][NH2:54])=[CH:48][CH:47]=1.CC(C)N=C=NC(C)C>CN(C=O)C>[C:1]([O:5][C:6](=[O:35])[CH2:7][CH:8]([C:9](=[O:11])[NH:54][CH2:53][CH2:52][C:49]1[CH:50]=[CH:51][C:46]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[CH:47][CH:48]=1)[CH2:12][CH2:13][CH2:14][S:15][C:16]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 282102-(4-Biphenyl)ethylamineHCID 757711-HydroxybenzotriazoleHCID 69210030HCID 69210030, compound

Product 1

HCID 69211444HCID 69211444, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound of example 29 (200 mg, 0.41 mmol) and HOBt (66 mg, 0.49 mmol) in DMF (2 mL), were added 4-biphenylethylamine (124 mg, 0.62 mmol) and DIC (78 μL) respectively. The reaction mixture was stirred for 24 h at room temperature. The reaction mixture was partitioned between HCl (0.5N, excess) and ethyl acetate. The aqueous phase was extracted several times with ethyl acetate. The recombined organic layer was washed with brine, with a saturated sodium hydrogen carbonate solution, and again with brine. The solvent was evaporated following drying over sodium sulfate, and the crude was flashed using 30% ethyl acetate in hexanes. 1H-NMR (CDCl3, 400 MHz: 1.55(s, 9H); 1.41-1.57(m, 2H); 2.04-2.28(m, 6H); 2.54(m, 1H); 2.80(m, 2H); 3.45-3.55(m, 2H), 5.66(m, 1H); 7.19-7.57(m, 24H).

Workup

  1. customThe reaction mixture was partitioned between HCl (0.5N, excess) and ethyl acetate
  2. extractionThe aqueous phase was extracted several times with ethyl acetate
  3. washThe recombined organic layer was washed with brine, with a saturated sodium hydrogen carbonate solution
  4. customThe solvent was evaporated
  5. dry with materialfollowing drying over sodium sulfate

Sources & evidence

ORD record
ord-690e1d6201194304acee7a9d792a0534
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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