Diisopropylethylamine → HCID 86762441, compound

HRID 1025334Notes

Reaction equation

HRID 1025334 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[CH3:23])(=[O:15])=[O:14])[CH2:10][C@H:9]1[C:24]([OH:26])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[NH2:29][C@@H:30]([CH2:39][CH3:40])[C@H:31]([OH:38])[C:32]([NH:34][CH:35]1[CH2:37][CH2:36]1)=[O:33].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:35]1([NH:34][C:32](=[O:33])[C@@H:31]([OH:38])[C@@H:30]([NH:29][C:24]([C@@H:9]2[CH2:10][C@@H:11]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=3[CH3:23])(=[O:15])=[O:14])[CH2:12][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:26])[CH2:39][CH3:40])[CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66771102HCID 66771102, compoundHCID 86762404(2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide dihydrochloride

Product 1

HCID 86762441HCID 86762441, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S,4R)-1-(tert-butoxycarbonyl)-4-(2,4-dimethylphenylsulfonyl)pyrrolidine-2-carboxylic acid (120 mg, 313 μmol, Eq: 1.00, prepared as described in U.S. Pat. Appl. US20100267722), (2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide dihydrochloride (99.7 mg, 407 μmol, Eq: 1.3), N,N-diisopropylethylamine (121 mg, 164 μA, 939 μmol, Eq: 3) and HATU (202 mg, 532 μmol, Eq: 1.7) were combined with DMF (2 ml) to give a light brown solution. The reaction was stirred overnight at RT. The crude material was purified by preparative HPLC (column: ymc C18 (120 A), 75×30 mm, acetonitrile/water (+0.1% formic acid)=95%-5% to 5%-95% in 8 min, flow: 25 ml/min). After evaporation of solvents, the title compound was obtained as a light brown foam (64.3 mg, 38.2%, MS (m/e)=538.3 [M+H+]).

Workup

  1. customto give a light brown solution
  2. customThe crude material was purified by preparative HPLC (column
  3. waitymc C18 (120 A), 75×30 mm, acetonitrile/water (+0.1% formic acid)=95%-5% to 5%-95% in 8 min
  4. customAfter evaporation of solvents

Sources & evidence

ORD record
ord-436a9d74c85f4792863bc172de5583de
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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