Chloroacetyl chloride → HCID 58300057, compound

HRID 876047Notes

Reaction equation

HRID 876047 reaction equation
C(N(CC)CC)C.Cl[CH2:9][C:10](Cl)=[O:11].[NH2:13][C:14]1([CH2:27][OH:28])[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1.CC(C)([O-])C.[K+]>C1COCC1.C(Cl)Cl>[C:21]1([CH2:20][N:17]2[CH2:18][CH2:19][C:14]3([NH:13][C:10](=[O:11])[CH2:9][O:28][CH2:27]3)[CH2:15][CH2:16]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 22020939HCID 22020939, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 58300057HCID 58300057, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

Triethylamine (2 mL 14 mmol) was added to a DCM (50 mL) solution containing chloroacetyl chloride (1 mL, 14 mmol) and compound 391 (3 g, 14 mmol). The resulting mixture was stirred 2 h at 23° C. The solvent was stripped and THF was added followed by potassium tert-butoxide (5 g, 41 mmol). The resulting solution was stirred overnight at room temperature. The reaction was then concentrated to dryness and the resulting residue was washed with 200 mL of absolute ethanol. The ethanolic solution was then concentrated to give 3.16 g of 9-(phenylmethyl)-4-oxa-1,9-diazaspiro[5.5]undecan-2-one. The material was used in the next step without further purification. LCMS-ESI (POS), M/Z, M+1: Found 261, Calculated 261.

Workup

  1. stirringThe resulting solution was stirred overnight at room temperature
  2. concentrationThe reaction was then concentrated to dryness
  3. washthe resulting residue was washed with 200 mL of absolute ethanol
  4. concentrationThe ethanolic solution was then concentrated

Sources & evidence

ORD record
ord-28b50f49557d4f7db984bef6f4f3379e
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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