Sodium Bicarbonate → HCID 86737784, compound

HRID 1680249Notes

Reaction equation

HRID 1680249 reaction equation
[OH:1][C:2]1[C:15]2[C@:14]34[CH2:16][CH2:17][NH:18][C@@H:8]([C@@H:9]3[CH2:10][C@H:11]([CH3:20])[C:12](=[O:19])[CH2:13]4)[CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:21][CH3:22].[CH:23]1([CH2:27]Br)[CH2:26][CH2:25][CH2:24]1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH:23]1([CH2:27][N:18]2[CH2:17][CH2:16][C@@:14]34[C:15]5[C:2]([OH:1])=[C:3]([O:21][CH3:22])[CH:4]=[CH:5][C:6]=5[CH2:7][C@@H:8]2[C@@H:9]3[CH2:10][C@H:11]([CH3:20])[C:12](=[O:19])[CH2:13]4)[CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734658(Bromomethyl)cyclobutaneHCID 86737779HCID 86737779, compound

Product 1

HCID 86737784HCID 86737784, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared by reaction of 18a (3.70 g, 12.3 mmole) with cyclobutylmethyl bromide (2.24 g, 14.7 mmole) in the presence of NaHCO3 (2.00 g, 25 mmole) in DMF (50 ml) at 100° under argon for 6 hours to give, after processing in the usual manner, 4.50 g (99%) of 19a-CBM as a foam. NMR: δ 6.60; 2H, s (aromatic); 5.5, 1H, broad (hydroxyl), 4.24, 1H, d (H-5α, J=13 Hz); 3.76 (CH3O--), 0.86, 3H, d(7α-CH3, J=6.5 Hz).

Workup

  1. customto give

Sources & evidence

ORD record
ord-3e4aed7d06a744ba9f2940755648f6bd
Source dataset
uspto-grants-1981_06
Patent number
US04272541

Reaction notes

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