Triethylamine → HCID 15016693, compound

HRID 1651177Notes

Reaction equation

HRID 1651177 reaction equation
[NH2:1][CH2:2][CH2:3][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.[CH3:22][CH:23]([CH3:28])[CH2:24][C:25](Cl)=[O:26].C(N(CC)CC)C>C(Cl)Cl>[CH3:22][CH:23]([CH3:28])[CH2:24][C:25]([NH:1][CH2:2][CH2:3][C@H:4]([OH:21])[C@@H:5]([NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66054Isovaleryl chlorideHCID 15016692HCID 15016692, compound

Product 1

HCID 15016693HCID 15016693, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To (3S,4S)-1-amino-3-hydroxy-4-t-butyloxycarbonylamino-5-cyclohexylpentane (30.8 mg, 0.102 mmol) in dry methylene chloride (3 mL) at 0° C. was added 3-methyl-butyroyl chloride (0.123 mmol) and triethylamine (20.0 microliters, 0.143 mmol). The mixture was stirred at 0° C. for 1 hour, evaporated, taken up in methanol (3 mL) and treated with 1 M NaOH (1 mL). After stirring for 1 hour, the mixture was diluted with ether, washed sequentially with 0.5M H3PO4, saturated NaHCO3 solution, and brine, and then dried over Na2SO4 and evaporated to afford the desired product.

Workup

  1. customevaporated
  2. additiontreated with 1 M NaOH (1 mL)
  3. stirringAfter stirring for 1 hour
  4. additionthe mixture was diluted with ether
  5. washwashed sequentially with 0.5M H3PO4, saturated NaHCO3 solution, and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-2d67d7e4ea164465a382cf2793b50a43
Source dataset
uspto-grants-1990_05
Patent number
US04927807

Reaction notes

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