Methanol → HCID 56594761, compound

HRID 1174166Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[C@@H:3]([OH:21])[CH2:4][C@@H:5]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:30]([O:37][C:38](ON1C(=O)CCC1=O)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(CC)C(C)C)(C)C.CO>C1COCC1.C(Cl)(Cl)Cl>[C:16]([O:15][C:14]([NH:13][C@@H:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:4][C@H:3]([OH:21])[C@@H:2]([NH:1][C:38](=[O:39])[O:37][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=1)=[O:20])([CH3:19])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution containing the product from Example 23F (6.1 g, 15.2 mmol) in THF (150 mL) was treated with N-(benzyloxycarbonyloxy)succinimide (3.4 g, 13.6 mmol) and N,N-diisopropylethylamine (3.3 mL, 19.0 mmol), stirred at 25° C. for 68 hours and concentrated. The residue was chromatographed on silica gel eluting with 33% ethyl acetate in chloroform and then with 10% methanol in chloroform to give the title compound (5.1 g, 63% yield).

Workup

concentrationconcentrated
customThe residue was chromatographed on silica gel eluting with 33% ethyl acetate in chloroform

Sources & evidence

ORD record: ord-956bfe160cc946da8d715ece7b93b9b3
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834043B2

Reaction notes

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