Dimethylformamide → HCID 178453625, compound

HRID 1979965Notes

Reaction equation

HRID 1979965 reaction equation
[Br-].[Na+].C(N(CC)CC)C.[C:10]([O:14][C:15]([NH:17][CH2:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([C:25]([OH:27])=[O:26])[CH2:21][CH2:20]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[CH3:28][N:29]([CH3:32])[CH:30]=[O:31]>>[C:10]([O:14][C:15]([NH:17][CH2:18][C@H:19]1[CH2:20][CH2:21][C@H:22]([C:25]([OH:27])=[O:26])[CH2:23][CH2:24]1)=[O:16])([CH3:13])([CH3:11])[CH3:12].[C:10]([O:14][C:15]([NH:17][CH2:18][C@H:19]1[CH2:20][CH2:21][C@H:22]([C:25]([OH:27])=[O:26])[CH2:23][CH2:24]1)=[O:16])([CH3:13])([CH3:11])[CH3:12].[OH:14][CH:15]([OH:16])[C:30]([N:29]([CH3:32])[CH3:28])=[O:31]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 253881Sodium BromideHCID 178453624HCID 178453624, compound

Product 1

HCID 178453625HCID 178453625, compound

Procedure

Sodium bromide (10.2 g; 0.1 mol) and 1,1-dichloro-N,N-dimethylacetamide (7.8 g; 0.05 mol) was added to dry dimethylformamide (100 ml) and the mixture was stirred for 4 h. Triethylamine (20.7 g; 0.2 mol) and trans-4-(tert.-butyloxycarbonylaminomethyl)cyclohexanecarboxylic acid (25.7 g; 0.1 mol) dissolved in dimethylformamide was added. The mixture was stirred for 84 h at 50° C. The solvent was evaporated and the residue was taken up into diethylether and washed, dried and evaporated. The oily residue was stirred with pentane. Yield 7 g, m.p. 110° C.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 84 h at 50° C
  3. customThe solvent was evaporated
  4. washwashed
  5. customdried
  6. customevaporated
  7. stirringThe oily residue was stirred with pentane

Sources & evidence

ORD record
ord-a4753816c331496e8f664ec8ef7c6e6e
Source dataset
uspto-grants-1984_11
Patent number
US04483867

Reaction notes

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