Diisopropylethylamine → HCID 59386542, compound

HRID 2358362Notes

Reaction equation

HRID 2358362 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][N:37]([CH2:50][CH2:51][CH2:52][CH:53]=[CH2:54])[S:38]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[N+:47]([O-:49])=[O:48])(=[O:40])=[O:39])[C:33](O)=[O:34])=[O:30])([CH3:27])([CH3:26])[CH3:25].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>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][N:37]([CH2:50][CH2:51][CH2:52][CH:53]=[CH2:54])[S:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[N+:47]([O-:49])=[O:48])(=[O:40])=[O:39])[C@H: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 58798664HCID 58798664, compoundHCID 59386549HCID 59386549, compound

Product 1

HCID 59386542HCID 59386542, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (2S,4R)-methyl 4-(biphenyl-4-yl)-4-methoxypyrrolidine-2-carboxylate (100 mg, 0.287 mmol), (S)-2-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoic acid (145 mg, 0.316 mmol), Hunig's Base (0.176 mL, 1.01 mmol) and HATU (131 mg, 0.345 mmol) in DCM (3 mL) was stirred at rt for 18 h. It was then concentrated in vacuo. The residue was dissolved in EtOAc and washed with dilute HCl, followed by sat.aq. NaHCO3 and water. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to yield 250 mg of the crude product as a brown oil. Purification by Biotage eluting with 60% EtOAc/Hexane gave 188 mg (87%) of (2S,4R)-methyl 4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoyl)-4-methoxypyrrolidine-2-carboxylate as an off-white foam.

Workup

  1. concentrationIt was then concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with dilute HCl
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield 250 mg of the crude product as a brown oil
  8. customPurification by Biotage
  9. washeluting with 60% EtOAc/Hexane

Sources & evidence

ORD record
ord-0ea134d149604b3d81671d7a40819f61
Source dataset
uspto-grants-2010_07
Patent number
US07763584B2

Reaction notes

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