Acetyl chloride → HCID 67642889, compound

HRID 469914Notes

Reaction equation

HRID 469914 reaction equation
[NH2:1][C@H:2]1[C@@H:7]2[C@@H:5]([C@H:6]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@:4]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:3]1[CH2:30][S:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[C:34]([CH3:39])[CH:33]=1.C(N(CC)CC)C.[C:47](Cl)(=[O:49])[CH3:48]>ClCCl>[C:47]([NH:1][C@H:2]1[C@@H:7]2[C@@H:5]([C@H:6]2[C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[C@:4]([NH:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[C@@H:3]1[CH2:30][S:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[C:34]([CH3:39])[CH:33]=1)(=[O:49])[CH3:48]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86665756HCID 86665756, compound

Product 1

HCID 67642889HCID 67642889, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-amino-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]bicyclo[3.1.0]hexane-2,6-dicarboxylate (0.15 g, 264.67 μmol) is dissolved in dichloromethane (10 mL). To this mixture is added triethylamine (55.34 μL, 397.01 μmol) and acetyl chloride (28.25 μL, 397.01 μmol). The mixture is stirred at ambient temperature for 10 minutes. The solvent is removed under reduced pressure to give a residue. The residue is purified by flash chromatography (10% to 100% ethyl acetate/hexanes) to give the title compound (100 mg, 164.27 μmol, 62.06% yield); 1H NMR (CD3Cl) δ 1.44 (t, 27H), 1.95 (s, 3H), 2.16 (m, 1H), 2.22 (s, 3H), 2.60 (dd, 1H), 2.78 (bs, 1H), 3.10 (dd, 1H), 4.59 (m, 1H), 5.50 (d, 1H), 6.92 (t, 1H), 7.06 (m, 1H), 7.11 (d, 1H).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customto give a residue
  3. customThe residue is purified by flash chromatography (10% to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-02bb314505c743049f6bf1767cea4494
Source dataset
uspto-grants-2014_01
Patent number
US08629169B2

Reaction notes

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