Triethylamine → HCID 56983237, compound

HRID 1722669Notes

Reaction equation

HRID 1722669 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]([CH3:29])[CH2:24][CH2:25][C:26](Cl)=[O:27].C(N(CC)CC)C>C(Cl)Cl>[CH3:22][CH:23]([CH3:29])[CH2:24][CH2:25][C:26]([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:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 170008Pentanoyl chloride, 4-methyl-HCID 15016692HCID 15016692, compound

Product 1

HCID 56983237HCID 56983237, compoundYield 100.8%

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 4-methylpentanoyl chloride (17.0 microliters, 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 1M 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 41.0 mg (100%) of the desired product as an oil.

Workup

  1. customevaporated
  2. additiontreated with 1M 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-e61e62aed9ea4f3b8ab836946be2d6e7
Source dataset
uspto-grants-1989_08
Patent number
US04857507

Reaction notes

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