Methanol → HCID 14346528, compound

HRID 1493753Notes

Reaction equation

HRID 1493753 reaction equation
B(Br)(Br)[Br:2].Cl.Cl.C[O:8][C:9]1[C:10]([CH3:41])=[C:11]([CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35]C)=[C:31]([O:37]C)[C:30]=2[CH2:39][CH3:40])[CH:12]=[CH:13][C:14]=1[O:15]C.CO>ClCCl>[BrH:2].[BrH:2].[OH:8][C:9]1[C:10]([CH3:41])=[C:11]([CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][C:29]2[C:30]([CH2:39][CH3:40])=[C:31]([OH:37])[C:32]([OH:35])=[CH:33][CH:34]=2)[CH:12]=[CH:13][C:14]=1[OH:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 14346526HCID 14346526, compound

Product 1

HCID 14346528HCID 14346528, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide (1.2 ml) in dichloromethane (10 ml) was added dropwise under nitrogen to a stirred, cooled solution of the product from Stage (i) (1.2 g) in dry dichloromethane (100 ml) at 0°. The mixture was stirred at room temperature for 5 h and methanol was then added. The mixture was evaporated in vacuo to give a solid which was recrystallised from methanol/ethyl acetate to give the title compound as a white powder (1 g), m.p. 178°-180°.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customto give a solid which
  3. customwas recrystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-9e9bee58c149473c84b918a26ee4601b
Source dataset
uspto-grants-1991_06
Patent number
US05023378

Reaction notes

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