HCID 86750109, compound → HCID 86750111, compound

HRID 1377853Notes

Reaction equation

C[O:2][C:3]([C@H:5]1[NH:17][C:16](=[S:18])[CH2:15][CH2:14][C@@H:13]([CH2:19][OH:20])[O:12][C:11](=[O:21])[C:10]2[C:22]([CH3:29])=[C:23]([O:27][CH3:28])[CH:24]=[C:25]([OH:26])[C:9]=2[CH2:8][S:7][CH2:6]1)=O>CO.C(N)C#C>[CH2:16]([NH:17][C:3]([C@H:5]1[NH:17][C:16](=[S:18])[CH2:15][CH2:14][C@@H:13]([CH2:19][OH:20])[O:12][C:11](=[O:21])[C:10]2[C:22]([CH3:29])=[C:23]([O:27][CH3:28])[CH:24]=[C:25]([OH:26])[C:9]=2[CH2:8][S:7][CH2:6]1)=[O:2])[C:15]#[CH:14]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 45 mg of the product of Example 12 in a mixture of 1 ml of methanol and 1 ml of prop-2-ynylamine was heated to 50° C. for 5 h. The mixture was evaporated in vacuo and the residual oil was chromatographed on silica gel using ethyl acetate/hexane (1:1, v/v) as eluent. The purified product was crystallized from ethyl acetate/hexane to yield 12 mg of (4R,9S)-15-hydroxy-9-hydroxymethyl-13-methoxy-12-methyl-11-oxo-6-thioxo-3,4,5,6,7,8,9,11-octahydro-1H-10,2,5-benzoxathiaazacyclotridecine-4-carboxylic acid prop-2-ynylamide as a white solid.

Workup

customThe mixture was evaporated in vacuo
customthe residual oil was chromatographed on silica gel
customThe purified product was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record: ord-a2b03efdb8f3433192e084107ab40472
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05665746

Reaction notes

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