Acetyl chloride → HCID 18932924, compound

HRID 1597825Notes

Reaction equation

HRID 1597825 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([B:17]2[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]2)[CH:14]([CH3:16])[CH3:15])=[O:11])[C:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:4][CH:3]=1.C(N(CC)CC)C.[C:39](Cl)(=[O:41])[CH3:40]>ClCCl>[C:39]([NH:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([B:17]2[O:21][C:20]([CH3:22])([CH3:23])[C:19]([CH3:25])([CH3:24])[O:18]2)[CH:14]([CH3:16])[CH3:15])=[O:11])[C:5]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[N:4][CH:3]=1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 18932915HCID 18932915, compound

Product 1

HCID 18932924HCID 18932924, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Example 2 (0.30 g) in dichloromethane (7 mL) was added triethylamine (0.11 mL) and acetyl chloride (55 uL). The reaction mixture was stirred overnight at room temperature. Evaporation gave a green-grey foam which was purified by chromatography, with chloroform:methanol (gradient, 50:1, 30:1) as the eluent, to yield the title compound (0.19 g) as a white powder; TLC: Rf =0.35, methanol:chloroform (5:95); NMR: 0.84 (d,3, J=6.7), 0.85 (d,3, J=6.8), 1.17 (s,12), 1.7-1.8 (m,1), 2.15 (s,3), 2.66 (t,1), 4.48 (s,2), 7.46-7.55 (m,5), 8.29 (d,1, J=5), 8.82 (s,1), 9.54 (s,1); MS: m/z=469(M+1). Analysis for C24H33BN4O5 : Calculated: C, 61.55; H, 7.10; N, 11.96; Found: C, 61.55; H, 7.23; N, 11.56.

Workup

  1. customEvaporation
  2. customgave a green-grey foam which
  3. customwas purified by chromatography, with chloroform

Sources & evidence

ORD record
ord-dd722fc3ecd7416b8df476d989c5f740
Source dataset
uspto-grants-1998_04
Patent number
US05736535

Reaction notes

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