Diisopropylethylamine → HCID 86670473, compound

HRID 1911857Notes

Reaction equation

HRID 1911857 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([NH2:9])[CH3:8].[C:10]([O:14][C:15]([N:17]1[C@@H:21]([C@H:22]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:20][CH2:19][C@H:18]1[CH2:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](O)=[O:43])=[CH:40][CH:39]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Si:30]([O:29][C@H:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C@H:21]1[CH2:20][CH2:19][C@@H:18]([CH2:37][C:38]2[CH:39]=[CH:40][C:41]([C:42](=[O:43])[NH:9][CH:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH3:8])=[CH:45][CH:46]=2)[N:17]1[C:15]([O:14][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:16])([C:33]([CH3:34])([CH3:35])[CH3:36])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5418771-(Pyridin-2-yl)ethan-1-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67971935HCID 67971935, compound

Product 1

HCID 86670473HCID 86670473, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Pyridin-2-yl-ethylamine (77 mg, 0.628 mmol) was added to a stirred, room temperature mixture of 4-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidin-2-yl}methyl)benzoic acid (300 mg, 0.571 mmol), HATU (260 mg, 0.685 mmol, 1.2 equivalents) and DIPEA (470 μL, 2.69 mmol, 4.7 equivalents) in DMF (1.2 mL). The reaction was stirred at room temperature for 16 hours before being loaded directly onto a silica column and purified by normal phase flash chromatography using silica gel (20-100% hexanes/ethyl acetate). The product fractions were collected and concentrated in vacuo to afford the title compound as a colorless gum (350 mg, 97%). LC-MS=630.3 (M+H)+.

Workup

  1. custompurified by normal phase flash chromatography
  2. customThe product fractions were collected
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26d406d927ea44a3bb063f51ebeccdf8
Source dataset
uspto-grants-2013_12
Patent number
US08604038B2

Reaction notes

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