Dimethylformamide → HCID 18655619, compound

HRID 742916Notes

Reaction equation

HRID 742916 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:10]([NH:12][C@H:13]([CH:21]([OH:42])[C@@H:22]([NH:30][C:31](=[O:41])[C@H:32]([CH:38]([CH3:40])[CH3:39])[NH:33][C:34](=[O:37])[CH2:35][NH2:36])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4].C(N([CH2:48][CH3:49])CC)C.[C:50](OC(=O)C)(=[O:52])[CH3:51].CN(C)C=[O:60]>O>[C:50]([NH:1][CH2:2][C:3]([NH:5][C@H:6]([C:10]([NH:12][C@H:13]([CH:21]([OH:42])[C@@H:22]([NH:30][C:31](=[O:41])[C@H:32]([CH:38]([CH3:40])[CH3:39])[NH:33][C:34](=[O:37])[CH2:35][NH:36][C:48](=[O:60])[CH3:49])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])[CH:7]([CH3:8])[CH3:9])=[O:4])(=[O:52])[CH3:51]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 18655613HCID 18655613, compound

Product 1

HCID 18655619HCID 18655619, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 200 mg (0.34 mmol) of the resultant compound of Example 141 and 98.4 μl (0.75 mmol) of triethylamine in 4 ml of dimethylformamide was treated with 68.0 μl (0.72 mmol) of acetic anhydride. After being stirred at ambient temperature for 2 h, the solution was diluted with water and extracted with four 10 ml portions of 10% methanol in dichloromethane. The combined organic layers were dried over MgSO4, and concentrated in vacuo. Silica gel chromatography of the residue using 10% methanol in dichloromethane provided 164.1 mg (72%) of the desired compound as a white solid. 1H NMR (DMSO-d6) δ0.69-0.81 (four d, 12H), 1.76 (m, 1H), 1.84 (two s, 6H), 1.92 (m, 1H), 2.60 (dd, 2H), 2.74 (br d, 2H), 2.97 (dd, 1H), 3.67 (d, 2H), 3.72 (d, 2H), 3.85 (m, 1H), 4.02 (m, 2H), 4.17 (dd, 1H), 5.24 (d, 1H), 7.07-7.26 (m, 10H), 7.46(br d, 1H), 7.53 (br d, 1H), 7.56 (br d, 1H), 7.72 (br d, 1H), 8.07 (br t, 1H), 8.12 (br t, 1H). Mass spectrum: (M+H)+ =667.

Workup

  1. extractionextracted with four 10 ml portions of 10% methanol in dichloromethane
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8dbeb0d639840fca08baeca896a16eb
Source dataset
uspto-grants-1996_09
Patent number
US05554783

Reaction notes

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