Trifluoroacetic acid → HCID 86726207, compound

HRID 1174259Notes

Reaction equation

[CH2:1]([C@H:8]([NH:40]C(=O)OC(C)(C)C)[CH2:9][C@H:10]([OH:39])[C@@H:11]([NH:26][C:27](=[O:38])[C@@H:28]([NH:33][C:34]([O:36][CH3:37])=[O:35])[C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:40][C@@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][C@H:10]([OH:39])[C@@H:11]([NH:26][C:27]([C@@H:28]([NH:33][C:34](=[O:35])[O:36][CH3:37])[C:29]([CH3:30])([CH3:32])[CH3:31])=[O:38])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution containing the product from Example 89B (0.302 mmol) in dichloromethane (2.5 mL) was treated with trifluoroacetic acid (2.5 mL), stirred at 25° C. for 16 hours and concentrated. The residue was purified by reversed phase chromatography on a C18 column eluting with 5-100% acetonitrile in water (0.1% TFA). The product was partitioned between ether and dilute ammonium hydroxide, and the organic phase was dried over MgSO4 filtered and concentrated to give the title compound (0.068 g, 42% yield).

Workup

concentrationconcentrated
customThe residue was purified by reversed phase chromatography on a C18 column
washeluting with 5-100% acetonitrile in water (0.1% TFA)
customThe product was partitioned between ether and dilute ammonium hydroxide
dry with materialthe organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-4ad1195157444906b3ece153754abf87
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834043B2

Reaction notes

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