Diisopropylethylamine → HCID 131722228, compound

HRID 1275894Notes

Reaction equation

HRID 1275894 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][C@H:11]([C:17]([O:19][CH3:20])=[O:18])[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:9])[N:6]=1.[CH3:21][C:22]1[CH:54]=[CH:53][C:25]2[CH:26]([C:36]3[C:37](=[S:52])[NH:38][C:39](=[O:51])[N:40]([CH2:42][C:43]4[O:47][C:46]([C:48](O)=[O:49])=[CH:45][CH:44]=4)[CH:41]=3)[C:27]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:28]=3[CH:29]=[CH:30][C:24]=2[CH:23]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH3:35][C:32]1[CH:33]=[CH:34][C:27]2[CH:26]([C:36]3[C:37](=[S:52])[NH:38][C:39](=[O:51])[N:40]([CH2:42][C:43]4[O:47][C:46]([C:48]([NH:1][C:2]5[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][C@H:11]([C:17]([O:19][CH3:20])=[O:18])[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:9])[N:6]=5)=[O:49])=[CH:45][CH:44]=4)[CH:41]=3)[C:25]3[CH:53]=[CH:54][C:22]([CH3:21])=[CH:23][C:24]=3[CH:30]=[CH:29][C:28]=2[CH:31]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 22117190HCID 22117190, compoundHCID 131722229HCID 131722229, compound

Product 1

HCID 131722228HCID 131722228, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of step (ii) (0.22 g), product of example 11(0.2 g), bromo-tris(pyrrolidino)-phosphonium hexafluorophosphate (0.24 g), 4-dimethylaminopyridine (0.056 g) and N,N-diisopropylethylamine (0.2 ml) in dimethylformamide (5 ml) was stirred at room temperature for 24 hours. The mixture was partitioned between ethyl acetate and brine, washed with saturated aqueous sodium bicarbonate, dilute HCl and brine, dried (MgSO4) and evaporated. Purification was by chromatography eluting with ethyl acetate. Yield 0.24 g.

Workup

  1. customThe mixture was partitioned between ethyl acetate and brine
  2. washwashed with saturated aqueous sodium bicarbonate, dilute HCl and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customPurification
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-34e06ab6bdb34e6ea424fed76dc57698
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Reaction notes

Loading…