Diisopropylethylamine → HCID 86715551, compound

HRID 630632Notes

Reaction equation

HRID 630632 reaction equation
CCN(C(C)C)C(C)C.Cl.[NH2:11][C@@H:12]([CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:13]([NH:15][C@@H:16]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:14].[O:39]1[CH2:44][CH2:43][N:42]([CH2:45][C:46](O)=[O:47])[CH2:41][CH2:40]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH3:29][CH:28]([CH3:30])[CH2:27][C@H:16]([NH:15][C:13](=[O:14])[C@@H:12]([NH:11][C:46](=[O:47])[CH2:45][N:42]1[CH2:43][CH2:44][O:39][CH2:40][CH2:41]1)[CH2:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4389684-Morpholineacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86715396HCID 86715396, compound

Product 1

HCID 86715551HCID 86715551, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Referring to FIG. 45. DIPEA (592 μL, 3.6 mmol, 2.6 eq) was added to a mixture of (S)-benzyl 2-((S)-2-amino-4-phenylbutanamido)-4-methylpentanoate hydrochloride (600 mg, 1.4 mmol), 2-morpholinoacetic acid (312 mg, 2.1 mmol, 1.5 eq) and HATU (816 mg, 2.1 mmol. 1.5 eq) in CH2Cl2 (25 mL) and the mixture was stirred overnight at RT. The reaction mixture was washed with water and the aqueous layer was extracted once with CH2Cl2. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (SiO2, 0-100% EtOAc in heptanes, followed by 10% MeOH in EtOAc) to yield product (700 mg, 98%) as a yellow oil.

Workup

  1. washThe reaction mixture was washed with water
  2. extractionthe aqueous layer was extracted once with CH2Cl2
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (SiO2, 0-100% EtOAc in heptanes, followed by 10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-f68fec7ff8a64a4bb57a9ba3a67a5477
Source dataset
uspto-grants-2016_04
Patent number
US09315542B2

Reaction notes

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