Acetic Acid → HCID 9833296, compound

HRID 380180Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:69])[NH:10][CH:11]([C:37](=[O:68])[N:38]([CH2:53][C:54]1[CH:59]=[CH:58][C:57]([O:60][CH2:61][C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[CH:56][CH:55]=1)[CH2:39][C:40](=[O:52])[NH:41][CH2:42][C:43]([CH3:51])([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH3:44])[CH2:12][C:13]1[N:14](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:15]=[N:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>O>[CH2:1]([O:8][C:9](=[O:69])[NH:10][C@H:11]([C:37](=[O:68])[N:38]([CH2:53][C:54]1[CH:55]=[CH:56][C:57]([O:60][CH2:61][C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[CH:58][CH:59]=1)[CH2:39][C:40](=[O:52])[NH:41][CH2:42][C:43]([CH3:51])([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH3:44])[CH2:12][C:13]1[NH:14][CH:15]=[N:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of the trityl compound from Step 5 (2.25 g, 2.4 mmol) was added glacial acetic acid (20 mL) and water (5 mL). The mixture was stirred at 90° C. for 30 minutes, then cooled and concentrated. The residue was taken up in ethyl acetate. The organic solution was washed twice with saturated NaHCO3, brine, and dried over MgSO4. The solution was concentrated and the compound purified by flash chromatography (0%-8% methanol in methylene chloride) to give the title compound (1.5 g, 2.2 mmol, 93%) as a white foam; ES-MS 674 (m+1).

Workup

temperaturecooled
concentrationconcentrated
washThe organic solution was washed twice with saturated NaHCO3, brine
dry with materialdried over MgSO4
concentrationThe solution was concentrated
customthe compound purified by flash chromatography (0%-8% methanol in methylene chloride)

Sources & evidence

ORD record: ord-304415049b3e4bfcbffb5eb7251f3f5f
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300501B1

Reaction notes

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