Acetyl chloride → HCID 53868563, compound

HRID 1004530Notes

Reaction equation

HRID 1004530 reaction equation
[NH2:1][CH:2]([C:22]1[CH:31]=[CH:30][C:29]2[C:28]([CH3:33])([CH3:32])[CH2:27][CH2:26][C:25]([CH3:35])([CH3:34])[C:24]=2[CH:23]=1)[C:3]([NH:5][C:6]1[CH:21]=[CH:20][C:9]([C:10]([O:12]CC2C=CC=CC=2)=[O:11])=[CH:8][CH:7]=1)=[O:4].C1C[O:39][CH2:38][CH2:37]1.C(N(CC)CC)C.C(Cl)(=O)C>O>[C:38]([NH:1][CH:2]([C:22]1[CH:31]=[CH:30][C:29]2[C:28]([CH3:33])([CH3:27])[CH2:32][CH2:34][C:25]([CH3:26])([CH3:35])[C:24]=2[CH:23]=1)[C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:20][CH:21]=1)=[O:4])(=[O:39])[CH3:37]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 15817220HCID 15817220, compound

Product 1

HCID 53868563HCID 53868563, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.5 g (3.2 mmol) of benzyl 4-[α-amino-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acetamido]benzoate, 75 ml of THF and 490 μl (3.5 mmol) of triethylamine were introduced into a round-bottomed flask. 250 μl (3.5 mmol) of acetyl chloride were added dropwise and the mixture was stirred at room temperature for 2 hours. The reaction medium was poured into water, extracted with ethyl acetate, the organic phase decanted, dried over magnesium sulfate and evaporated. The residue obtained was triturated in hexane, filtered and dried. 1.6 g (94%) of the expected compound of melting point 258°-259° C. was obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase decanted
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas triturated in hexane
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-e186a9126e2548ddb037547a7bb57492
Source dataset
uspto-grants-2000_04
Patent number
US06051243

Reaction notes

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