Diisopropylethylamine → HCID 57988422, compound

HRID 2081138Notes

Reaction equation

HRID 2081138 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][C:14]([N:16]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][C:22]=3[Cl:25])[CH2:17]2)=[O:15])[CH2:10][C@H:9]1[C:26](O)=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[NH2:31][C@:32]1([C:37]([NH:39][S:40]([CH:43]2[CH2:45][CH2:44]2)(=[O:42])=[O:41])=[O:38])[CH2:34][C@H:33]1[CH2:35][CH3:36].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.OS([O-])(=O)=O.[K+]>C(Cl)Cl.O>[Cl:25][C:22]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:23]=1[CH2:24][N:16]([C:14]([O:13][C@@H:11]1[CH2:10][C@@H:9]([C:26](=[O:27])[NH:31][C@:32]3([C:37](=[O:38])[NH:39][S:40]([CH:43]4[CH2:45][CH2:44]4)(=[O:42])=[O:41])[CH2:34][C@H:33]3[CH2:35][CH3:36])[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:12]1)=[O:15])[CH2:17]2

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 516920Potassium bisulfateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57437882HCID 57437882, compoundHCID 67103233HCID 67103233, compound

Product 1

HCID 57988422HCID 57988422, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(2S,4R)-1-(tert-butoxycarbonyl)-4-(4-chloroisoindoline-2-carbonyloxy)pyrrolidine-2-carboxylic acid (0.93 g, 2.26 mmol), (1R,2R)-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide dihydrochloride (0.64 g, 2.38 mmol) and HATU (0.79 g, 2.078 mmol) in DCM (20 mL) was added DIEA (1.18 ml, 6.79 mmol) and the reaction was stirred at rt for 18 hours. H2O (10 mL) was added and acidified with saturated KHSO4 until PH=3˜4. The mixture was extracted with ether (30 mL), washed with brine and dried over sodium sulfate. After removal of solvent, it gave (3R,5S)-1-(tert-butoxycarbonyl)-5-((1R,2R)-1-(cyclopropylsulfonylcarbamoyl)-2-ethylcyclopropylcarbamoyl)pyrrolidin-3-yl 4-chloroisoindoline-2-carboxylate (1.36 g, 96%) as a white solid, which was used directly for the next step without purification. LCMS (APCI+): 525.1 (MH+−Boc).

Workup

  1. extractionThe mixture was extracted with ether (30 mL)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent, it

Sources & evidence

ORD record
ord-ec35314446954d289527cdde3d063a27
Source dataset
uspto-grants-2011_04
Patent number
US07932277B2

Reaction notes

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