Tetrabutylammonium Fluoride → benzyl (1S,3S,4S)-4-[(tert-butoxymethyl)amino]-3-hydroxy-1-[4-(6-methoxy-2-pyridinyl)benzyl]-5-phenylpentylcarbamate

HRID 1174310Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C@@H:10]([O:39][Si](C(C)(C)C)(C)C)[CH2:11][C@@H:12]([NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[N:21]=2)=[CH:16][CH:15]=1)=O)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][CH2:6][NH:8][C@@H:9]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C@@H:10]([OH:39])[CH2:11][C@@H:12]([NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[N:21]=2)=[CH:16][CH:15]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

The product from Example 113B (0.28 mmol) was treated with TBAF solution in THF (1.4 mL, 1N), stirred at 25° C. for 16 hours, concentrated and partitioned between ethyl acetate and water. The organic phase was washed with brined, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 20% ethyl acetate in dichloromethane, to give the title compound (0.055 g, 31% yield).

Workup

concentrationconcentrated
custompartitioned between ethyl acetate and water
washThe organic phase was washed with brined,
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was chromatographed on silica gel eluting with 20% ethyl acetate in dichloromethane

Sources & evidence

ORD record: ord-7728d5d305be4ef6a176583305f3677e
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834043B2

Reaction notes

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