Acetyl chloride → HCID 10440854, compound

HRID 2396610Notes

Reaction equation

HRID 2396610 reaction equation
CCN(CC)CC.[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([O:64][CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:22](=[O:63])[CH2:23][CH2:24][C:25](=[O:62])[NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:32]([O:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:33](=[O:53])[CH2:34][CH2:35][C:36](=[O:52])[NH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][NH:43][O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[C:72](Cl)(=[O:74])[CH3:73]>C(Cl)Cl>[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([O:64][CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:22](=[O:63])[CH2:23][CH2:24][C:25](=[O:62])[NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:32]([O:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:33](=[O:53])[CH2:34][CH2:35][C:36](=[O:52])[NH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][N:43]([O:44][CH2:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[C:72](=[O:74])[CH3:73])=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 10056534HCID 10056534, compound

Product 1

HCID 10440854HCID 10440854, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

NEt3 (0.16 mL, 1.15 mmol) was added to (11) (0.87 g, 0.98 mmol) in CH2Cl2 (40 mL) and the solution was cooled to 0° C. Acetyl chloride (0.074M in CH2Cl2, 14 mL, 1.04 mmol) was added by syringe over 4 minutes and stirring was continued (0° C. to room temperature) for 24 hours. The aqueous phase was extracted with CH2Cl2 (4×50 mL) and the organic phase was washed with 40 mL portions of cold 0.25M citric acid, 5% NaHCO3 and H2O. Solvent removal and flash column chromatography with 60% acetone/hexane gave 0.79 g (87%) of (12) as an oil: 300 MHz NMR δ 1.23-1.69 (m+s, 27 H), 2.09 (s, 3 H), 2.44-2.53 (m, 4 H), 2.76-2.84 (m, 6 H), 3.03-3.24 (m, 6 H), 3.57-3.68 (m, 6 H), 4.7 (br s, 1 H), 4.81 (s, 2 H), 4.85 and 4.86 (2 s, 4 H), 6.35 (br s, 1 H), 7.38 (s, 15 H). Anal. calcd. for C51H74N6O10 : C, 65.78; H, 8.01; N, 9.03. Found: C, 65.89; H, 8.04; N, 8.95.

Workup

  1. custom(0° C. to room temperature)
  2. customfor 24 hours
  3. extractionThe aqueous phase was extracted with CH2Cl2 (4×50 mL)
  4. washthe organic phase was washed with 40 mL portions of cold 0.25M citric acid, 5% NaHCO3 and H2O
  5. customSolvent removal and flash column chromatography with 60% acetone/hexane

Sources & evidence

ORD record
ord-5c967479306e4fbc9637181c143603d7
Source dataset
uspto-grants-1996_02
Patent number
US05493053

Reaction notes

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