Acetyl chloride → HCID 68542976, compound

HRID 1432089Notes

Reaction equation

HRID 1432089 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]([CH3:24])[CH2:15][C@@H:14]([C@@H:25]([OH:36])[CH2:26][C@H:27]([C:29](=[O:35])[NH:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH3:28])[NH:13][C:12](=[O:37])[C@H:11]([CH3:38])[NH:10][C:9]1=[O:39])(C)(C)C.[C:41](Cl)(=[O:43])[CH3:42]>Cl.O1CCOCC1>[C:41]([NH:7][C@@H:8]1[C:9](=[O:39])[NH:10][C@@H:11]([CH3:38])[C:12](=[O:37])[NH:13][C@H:14]([C@@H:25]([OH:36])[CH2:26][C@@H:27]([CH3:28])[C:29]([NH:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:35])[CH2:15][C@H:16]([CH3:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)(=[O:43])[CH3:42]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 68539439HCID 68539439, compound

Product 1

HCID 68542976HCID 68542976, compound

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 45 mg (0.079 mmol) [(3S,6S,14R,16S)-16-((1S,3R)-3-butylcarbamoyl-1-hydroxy-butyl)-3,14-dimethyl-2,5-dioxo-1,4diaza-cyclohexadec-6-yl]-carbamic acid tert-butyl ester (example 6) in 1 ml 4N HCl/dioxane is kept for 3 h and then evaporated. The residue is taken up in 3 ml THF and 1 ml EtOH and 1 ml 10% aqueous sodium carbonate, cooled to 0° C. and stirred vigorously. 0.112 ml (1.6 mmol) acetyl chloride are added and stirring is continued for 1 h. The solvents are evaporated and the residue is stirred with water and TBME/hexane for 30 min. The mixture is filtered to yield the title compound.

Workup

  1. customevaporated
  2. stirringstirring
  3. customThe solvents are evaporated
  4. stirringthe residue is stirred with water and TBME/hexane for 30 min
  5. filtrationThe mixture is filtered

Sources & evidence

ORD record
ord-b55bfff01f344c2a823d572a84e1bb40
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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