Diisopropylethylamine → HCID 86650281, compound

HRID 1889222Notes

Reaction equation

HRID 1889222 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[S:10])=[CH:4][CH:3]=1.[C:24]([O:28][C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37](O)=[O:38])=[O:30])([CH3:27])([CH3:26])[CH3:25].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:24]([O:28][C:29](=[O:30])[NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37](=[O:38])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12](=[O:23])[C:13]2[CH:14]=[CH:15][C:16]([C:19]([CH3:20])([CH3:22])[CH3:21])=[CH:17][CH:18]=2)=[S:10])=[CH:4][CH:3]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acidHCID 2733179PyBroPHCID 24772097Tenovin-3

Product 1

HCID 86650281HCID 86650281, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thiourea 4 (100 mg, 0.31 mmol, 1 equiv.) was stirred in dry CH2Cl2 (5 mL) under N2 atmosphere and acid 31 (106 mg, 0.46 mmol, 1.5 equiv.) was added, followed by bromo-tris-pyrrolidino phosphoniumhexafluorophosphate (214 mg, 0.46 mmol, 1.5 equiv.), and N,N-diisopropylethylamine (53 μL, 0.31 mmol, 1 equiv.). The reaction mixture was stirred at rt for 16 h then diluted with CH2Cl2 (20 mL) and washed with 1 M aqueous hydrochloric acid (1×10 mL), 1 M aqueous sodium hydroxide (1×10 mL), and saturated brine (1×10 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give a crude yellow oil which was purified with column chromatography on silica (25-50% ethyl acetate/petroleum ether) to give 32 (86 mg, 54%) as a colourless oil.

Workup

  1. washwashed with 1 M aqueous hydrochloric acid (1×10 mL), 1 M aqueous sodium hydroxide (1×10 mL), and saturated brine (1×10 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give a crude yellow oil which
  5. customwas purified with column chromatography on silica (25-50% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-a85a7685852241df9725fc8904fec06a
Source dataset
uspto-grants-2013_08
Patent number
US08501991B2

Reaction notes

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