Ammonia → HCID 69065297, compound

HRID 2221355Notes

Reaction equation

[CH3:1][C:2]1([CH3:27])[C@H:11]2[O:12][C@H:10]2[C:9]2[CH:8]=[C:7]([CH2:13][C:14]([NH:16][CH:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20][CH2:19][CH2:18]3)=[O:15])[CH:6]=[CH:5][C:4]=2[O:3]1.[NH3:28]>>[NH2:28][C@@H:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:13][C:14]([NH:16][C@H:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20][CH2:19][CH2:18]3)=[O:15])[CH:8]=2)[O:3][C:2]([CH3:27])([CH3:1])[C@H:11]1[OH:12]

Participants

Reactant 2

HCID 222Ammonia

HCID 86599515HCID 86599515, compound

Product 1

HCID 69065297HCID 69065297, compound

Procedure

40 g of the 2-[(1aS,7bS)-(2,2-dimethyl-1a,7b-dihydro-2H-oxireno[c]chromen-6-yl]-N-1,2,3,4-tetrahydronaphth-1-yl acetamide obtained above and 250 ml of a 25%-strength aqueous ammonia solution were reacted in a manner corresponding to the procedure of Example 1E). Chromatography of the crude product on silica gel (mobile phase: dichloromethane/methanol/25%-strength aqueous ammonia solution (75:50:2 v/v/v)) yielded 13.2 g 2-[(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl]-N-[(1R)-1,2,3,4-tetrahydronaphth-1-yl]acetamide as oil, which was used without further purification for the subsequent reaction.

Workup

customwere reacted in a manner corresponding to the procedure of Example 1E)

Sources & evidence

ORD record: ord-fc728e1852c94d988a48cdcb99f0ce4a
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368582B2

Reaction notes

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