Triethylamine → Carbamate

HRID 1852121

Reaction equation

HRID 1852121 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30]([NH:32][C@@H:33]([C@H:45]([CH3:53])[CH2:46][CH:47]([CH3:52])[CH2:48][CH2:49][CH:50]=[CH2:51])[C:34]([N:36]1[CH2:40][C@H:39]([OH:41])[CH2:38][C@H:37]1[C:42]([OH:44])=O)=[O:35])=[O:31])([CH3:28])([CH3:27])[CH3:26].Cl.[NH2:55][C@:56]1([C:61]([NH:63][S:64]([C:67]2([CH2:70][F:71])[CH2:69][CH2:68]2)(=[O:66])=[O:65])=[O:62])[CH2:58][C@H:57]1C=C.C(N(CC)CC)C>C(Cl)Cl>[F:71][CH2:70][C:67]1([S:64]([NH:63][C:61]([C@@:56]23[CH2:58][C@H:57]2[CH:51]=[CH:50][CH2:49][CH2:48][CH:47]([CH3:52])[CH2:46][C@@H:45]([CH3:53])[C@H:33]([NH:32][C:30](=[O:31])[O:29][C:25]([CH3:26])([CH3:28])[CH3:27])[C:34](=[O:35])[N:36]2[CH2:40][C@H:39]([OH:41])[CH2:38][C@H:37]2[C:42](=[O:44])[NH:55]3)=[O:62])(=[O:66])=[O:65])[CH2:68][CH2:69]1.[C:30](=[O:29])([O-:31])[NH2:32]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86683196(2S,4R)-1-((2S,3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acidHCID 86683199HCID 86683199, compound

Product 2

HCID 276CarbamateYield 1,959.7%HCID 71005415HCID 71005415, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HATU (11.61 g, 30.5 mmol) was added to a solution of (2S,4R)-1-((2S,3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acid (10.50 g, 25.5 mmol), (1R,2S)-1-amino-N-((1-(fluoromethyl)cyclopropyl)sulfonyl)-2-vinylcyclopropanecarboxamide HCl (8.37 g, 28 mmol), and triethylamine (14.19 mL, 102 mmol) in DCM (220 mL) and was stirred at RT for overnight. The reaction was washed with 1N HCl (3×) and then brine and evaporated on rotovap. The crude material was purified by silica gel chromatography using 20-40% Acetone in hexanes. The product fractions were collected and the solvent removed under vacuum to give the desired product tert-butyl ((2S,3R)-1-((2S,4R)-2-(1R,2S)-1-(((1-(fluoromethyl)cyclopropyl)sulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)-4-hydroxypyrrolidin-1-yl)-3,5-dimethyl-1-oxonon-8-en-2-yl)carbamate (15 g, 90% yield). MS: MS m/z 657.3 (M++1).

Workup

  1. washThe reaction was washed with 1N HCl (3×)
  2. custombrine and evaporated on rotovap
  3. customThe crude material was purified by silica gel chromatography
  4. customThe product fractions were collected
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-3622bbc10ce544599b9a5b1645adc8d7
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Linked notes

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