Triethylamine → HCID 131728676, compound

HRID 1363384Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:19][CH3:20])[CH:13]=[C:12]([O:21][CH3:22])[C:11]=2[C@@H:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH2:25][C@H:24]1[OH:37].CS(Cl)(=O)=O.C(N(CC)CC)C.[C:50]([O-])(=[O:52])[CH3:51].[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:19][CH3:20])[CH:13]=[C:12]([O:21][CH3:22])[C:11]=2[C@@H:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C@H:25]1[CH2:24][O:37][C:50](=[O:52])[CH3:51]

Participants

Reactant 4

HCID 8471Triethylamine

HCID 31297Methanesulfonyl chloride

HCID 517045Sodium Acetate

HCID 66933942HCID 66933942, compound

Product 1

HCID 131728676HCID 131728676, compound

Procedure

Compound of example 122 (1.7 g, 3.2 mmol) was subjected to ring contraction as described in example 3, method A using methanesulfonyl chloride (0.448 g, 0.3 mL, 3.9 mmol), triethylamine (0.66 g, 0.95 mL, 6.5 mmol). The sulfonyl ester was treated with anhydrous sodium acetate (1.06 g, 13 mmol) to furnish the title compound.

Sources & evidence

ORD record: ord-fa344e092cfa484aa622aa9a07c10cf8
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884127B2

Reaction notes

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