Triethylamine → HCID 14478729, compound

HRID 1904206Notes

Reaction equation

HRID 1904206 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:22])[C@H:4]([OH:21])[C@@H:5]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH3:23][CH:24]([CH3:30])[CH2:25][CH2:26][C:27](Cl)=[O:28].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[CH3:23][CH:24]([CH3:30])[CH2:25][CH2:26][C:27]([NH:1][CH2:2][C@H:3]([OH:22])[C@H:4]([OH:21])[C@@H:5]([NH:13][C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 170008Pentanoyl chloride, 4-methyl-HCID 14478727HCID 14478727, compound

Product 1

HCID 14478729HCID 14478729, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To the resultant compound from Example 9 (94.6 mg, 0.299 mmol) in methylene chloride ,(5 mL) at 0° C. was added 4-methylpentanoyl chloride (52 ul, 0.37 mmol) and triethylamine (71 ul, 0.51 mmol). The mixture was stirred at 0° C. for 90 min, diluted with ethyl acetate, washed sequentially with 0.5M H3PO4 solution, 2M NaOH solution and brine, and then dried over Na2SO4 and evaporated to afford 0.118 g (95%) of the desired compound, m.p. 179°-183° C.

Workup

  1. washwashed sequentially with 0.5M H3PO4 solution, 2M NaOH solution and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-e029c307d03f46b5945d9647743769d3
Source dataset
uspto-grants-1989_06
Patent number
US04837204

Reaction notes

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