Diisopropylethylamine → HCID 86702755, compound

HRID 526262Notes

Reaction equation

HRID 526262 reaction equation
[NH2:1][C@@H:2]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@@H:3]([NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH2:4][C:5]([NH:7][C@@H:8]([C@@H:20]([CH3:23])[CH2:21][CH3:22])[C:9]([NH:11][C@@H:12]([CH:17]([CH3:19])[CH3:18])[C:13]([O:15][CH3:16])=[O:14])=[O:10])=[O:6].[CH3:42][C:43]([CH3:64])([CH3:63])[C@H:44]([NH:48][C:49](=[O:62])[C@@H:50]([NH:55][C:56](=[O:61])[CH2:57][CH:58]([CH3:60])[CH3:59])[CH2:51][CH:52]([CH3:54])[CH3:53])[C:45](O)=[O:46].C(N(C(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(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:28]([O:27][C:25]([NH:24][C@H:3]([C@@H:2]([NH:1][C:45](=[O:46])[C@@H:44]([NH:48][C:49](=[O:62])[C@@H:50]([NH:55][C:56](=[O:61])[CH2:57][CH:58]([CH3:59])[CH3:60])[CH2:51][CH:52]([CH3:54])[CH3:53])[C:43]([CH3:63])([CH3:42])[CH3:64])[CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH2:4][C:5]([NH:7][C@@H:8]([C@@H:20]([CH3:23])[CH2:21][CH3:22])[C:9]([NH:11][C@@H:12]([CH:17]([CH3:19])[CH3:18])[C:13]([O:15][CH3:16])=[O:14])=[O:10])=[O:6])=[O:26])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86702754HCID 86702754, compoundHCID 86702756HCID 86702756, compound

Product 1

HCID 86702755HCID 86702755, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

300 mg of methyl (S)-2-[(2S,3S)-2-((3S,4S)-4-amino-3-benzyloxycarbonylamino-5-phenylpentanoylamino)-3-methylpentanoylamino]-3-methylbutyrate (hydrochloride), 170.1 mg of (S)-3,3-dimethyl-2-[(S)-4-methyl-2-(3-methylbutyrylamino)pentanoylamino]butyric acid and 163.4 l of ethyldiisopropylamine were dissolved in about 10 ml of DMF in a flask with ice cooling, 197.0 mg of HATU (C10H15N6O*PF6) were added, and the mixture was stirred at RT overnight. The yellow reaction mixture was poured into saturated sodium hydrogencarbonate solution and stirred for 15 min. The precipitate formed was filtered off with suction, triturated with dilute formic acid, filtered off with suction again, washed with water and dried, giving 340 mg of methyl (S)-2-[(2S,3S)-2-((3S,4S)-3-benzyloxycarbonylamino-4-{(S)-3,3-dimethyl-2-[(S)-4-methyl-2-(3-methylbutyrylamino)pentanoylamino]butyrylamino}-5-phenylpentanoylamino)-3-methylpentanoylamino]-3-methylbutyrate as a white solid. (Yield 82%). MS-FAB (M+H+)=880.1 Rf (polar method): 2.91 min.

Workup

  1. additionwere added
  2. stirringstirred for 15 min
  3. customThe precipitate formed
  4. filtrationwas filtered off with suction
  5. customtriturated with dilute formic acid
  6. filtrationfiltered off with suction again
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-42db8326089a44a38878e5bf2a9888f9
Source dataset
uspto-grants-2016_05
Patent number
US09345742B2

Reaction notes

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