Acetic Anhydride → HCID 44434818, compound

HRID 1271718Notes

Reaction equation

HRID 1271718 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C@H:10]2[C@@H:14]([NH:15][C:16](=[O:30])[C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]4=[O:29])=[CH:19][CH:18]=3)[CH2:13][NH:12][CH2:11]2)=[O:8])=[CH:4][CH:3]=1.CCN(CC)CC.[C:38](OC(=O)C)(=[O:40])[CH3:39]>C1COCC1>[C:38]([N:12]1[CH2:13][C@H:14]([NH:15][C:16](=[O:30])[C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]3=[O:29])=[CH:21][CH:22]=2)[C@H:10]([NH:9][C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:8])[CH2:11]1)(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11396607HCID 11396607, compound

Product 1

HCID 44434818HCID 44434818, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Example 75 (6 mg, 0.013 mmol) in THF (200 μl) at 0° C. was added Et3N (3 μl, 0.021 mmol) followed by the acetic anhydride (5 μl, 0.04 mmol). The reaction mixture was stirred at 0° C. for 5 minutes and then at rt for 10 minutes. The solvent was evaporated under pressure, and the residue was purified by preparative HPLC using 0 to 100% B over 10 minutes (Column, Luna 10μ, C18 25×100 mm; Solvent A, 10% ACN +90% H2O with 0.1% TFA; Solvent B, 90% ACN+10% H2O with 0.1% TFA) to afford the title compound (2.8 mg, 48%) as a white lyophilite. MS m/z 486 ([M+H]+).

Workup

  1. waitat rt for 10 minutes
  2. customThe solvent was evaporated under pressure
  3. customthe residue was purified by preparative HPLC
  4. customover 10 minutes

Sources & evidence

ORD record
ord-e4139c06e57147a29055b4c21359de1c
Source dataset
uspto-grants-2007_04
Patent number
US07205318B2

Reaction notes

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