Triethylamine → HCID 19390813, compound

HRID 1756712Notes

Reaction equation

HRID 1756712 reaction equation
C(OC([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:40]([CH3:42])[CH3:41])[CH:24]([OH:39])[C:25]([F:38])([F:37])[C:26](=[O:36])[NH:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:21])[C:15]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[N:14][CH:13]=1)=O)C1C=CC=CC=1.C(N(CC)CC)C.Cl.C(OC(=O)CN)(C)(C)C>O1CCCC1>[NH2:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:40]([CH3:42])[CH3:41])[C:24](=[O:39])[C:25]([F:38])([F:37])[C:26](=[O:36])[NH:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:21])[C:15]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[N:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 2725036Glycine tert-butyl ester hydrochloride2×HCID 19390818HCID 19390818, compound

Product 1

HCID 19390813HCID 19390813, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(5-Benzyloxycarbonylamino-6-oxo-2-phenyl-1,6-dihydropyrimidin-1-yl)-N-[3,3-difluoro-1-isopropyl-2-hydroxy-3-[N-(tert-butoxycarbonylmethyl)carbamoyl]propyl]acetamide. To a solution of the product described at Example 1.b. (1.05 g) in tetrahydrofuran (17 mL) was added triethylamine (0.82 mL) and glycine tert-butylester hydrochloride (0.990 g). After 18 hours, additional triethylamine (0.30 mL) and glycine tert-butylester hydrochloride (0.33 g) were added. The additions were repeated after 1 day, and the reaction mixture stirred for 1 day. The mixture was evaporated and the solids were triturated with water, collected by filtration, washed (water, ether, hexane), and dried under vacuum to yield the title compound as a white powder; TLC: Rf =0.47, chloroform:methanol (97:3); m/z=672(M+1).

Workup

  1. waitThe additions were repeated after 1 day
  2. customThe mixture was evaporated
  3. customthe solids were triturated with water
  4. filtrationcollected by filtration
  5. washwashed (water, ether, hexane)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-060b3a7c01854bd4b2aa86328b39d768
Source dataset
uspto-grants-1995_08
Patent number
US05441960

Reaction notes

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