Diisopropylethylamine → HCID 66752869, compound

HRID 2358358Notes

Reaction equation

HRID 2358358 reaction equation
[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][C:4]([C@@:7]2([O:16][CH3:17])[CH2:11][NH:10][C@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)=[CH:3][CH:2]=1.[C:24]([O:28][C:29]([NH:31][C@@H:32]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])[C:33](O)=[O:34])=[O:30])([CH3:27])([CH3:26])[CH3:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:2]=[CH:3][C:4]([C:7]2([O:16][CH3:17])[CH2:11][N:10]([C:33](=[O:34])[C@@H:32]([NH:31][C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])[CH:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)=[CH:5][CH:6]=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 11507316(2S)-N-Boc-amino-non-8-enoic acidHCID 59386549HCID 59386549, compound

Product 1

HCID 66752869HCID 66752869, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2S,4R)-methyl 4-(biphenyl-4-yl)-4-methoxypyrrolidine-2-carboxylate (150 mg, 0.482 mmol), (S)-2-(tert-butoxycarbonylamino)non-8-enoic acid (144 mg, 0.530 mmol), and HATU (260 mg, 0.723 mmol) in DCM (5 ml) was added N,N-diisopropylethylamine (0.252 ml, 1.445 mmol) at 0° C. The reaction mixture was allowed to warm to rt and was stirred for 18 h. It was then diluted with DCM, washed with 5% citric acid, and brine, dried(MgSO4), filtered, and concentrated in vacuo. The residue was purified by prep-HPLC to yield 2S,4R)-methyl 4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)non-8-enoyl)-4-methoxypyrrolidine-2-carboxylate (140 mg, 51.5% yield) as white foam.

Workup

  1. washwashed with 5% citric acid, and brine, dried(MgSO4)
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-652ac00ca94642858d6421c2c09fdcee
Source dataset
uspto-grants-2010_07
Patent number
US07763584B2

Reaction notes

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