Diisopropylethylamine → (S)-methyl 13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oate

HRID 2201717Notes

Reaction equation

HRID 2201717 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:4]([NH:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:5].[C:16]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](O)=[O:30])=[O:22])([CH3:19])([CH3:18])[CH3:17].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>C1COCC1>[CH2:12]([C@@H:3]([C:4](=[O:5])[NH:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])[NH:2][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][NH:23][C:21](=[O:22])[O:20][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18603049(S)-methyl 2-(2-amino-4-methylpentanamido)acetate hydrochloride

Product 1

HCID 86712539(S)-methyl 13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 2-(2-amino-4-methylpentanamido)acetate hydrochloride (4w) in THF was added 6-((tert-butoxycarbonyl)amino) hexanoic acid, HATU and DIPEA. The reaction was stirred at room temperature for 18 h. The mixture was then filtered through Celite. The filtrate was concentrated under reduced pressure and the crude residue was purified by column chromatography (silica gel, CH2Cl2/MeOH=50/1) to give (S)-methyl 13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oate (6w) as a white solid.

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe crude residue was purified by column chromatography (silica gel, CH2Cl2/MeOH=50/1)

Sources & evidence

ORD record
ord-eca421be126b4b3ebe261069333fcfa8
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

Loading…