Diisopropylethylamine → HCID 22262715, compound

HRID 1394831Notes

Reaction equation

HRID 1394831 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]([NH:17][C:18]3[CH:19]=[CH:20][C:21]4[O:25][C:24]([C:26]([OH:28])=O)=[CH:23][C:22]=4[CH:29]=3)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.Cl.[CH2:33]([NH:36][C:37](=[O:46])[C@H:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[NH2:39])[CH2:34][CH3:35].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[O:46]=[C:37]([NH:36][CH2:33][CH2:34][CH3:35])[CH:38]([NH:39][C:26]([C:24]1[O:25][C:21]2[CH:22]=[CH:29][C:18]([NH:17][C:15]([C:10]3[C:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:30])([F:31])[F:1])=[CH:8][CH:7]=4)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:16])=[CH:19][C:20]=2[CH:23]=1)=[O:28])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 12148809HCID 12148809, compoundHCID 68952632HCID 68952632, compound

Product 1

HCID 22262715HCID 22262715, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step (d) (100 mg, 0.235 mmol), (S)-N-propyl-2-phenylglycinamide hydrochloride salt (1 eq.) and PyBrop (1.1 eq.) were dissolved in CH2Cl2 (2 mL), followed by the addition of diisopropylethylamine (3 eq.), and the reaction mixture was stirred at room temperature between 2 hours. The solvent was then evaporated, and the product was purified by prep-TLC using 2:1 EtOAc/hexane as eluting solvent, and the yield was 79 mg.

Workup

  1. customThe solvent was then evaporated
  2. customthe product was purified
  3. washas eluting solvent

Sources & evidence

ORD record
ord-12514ed7dfc64ecb864bb191b1cfc370
Source dataset
uspto-grants-2008_03
Patent number
US07348355B2

Reaction notes

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