Ethanethiol → HCID 68575388, compound

HRID 1714824Notes

Reaction equation

HRID 1714824 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH:20]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][C:26]5[O:31][CH2:30][CH2:29][N:28]([CH2:32][CH2:33][CH2:34][O:35][CH3:36])[C:27]=5[CH:37]=4)[CH2:19][N:18](C(OCC4C=CC=CC=4)=O)[CH2:17][CH:16]3[OH:48])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.B(F)(F)F.CCOCC.C(S)C>ClCCl>[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH:20]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][C:26]5[O:31][CH2:30][CH2:29][N:28]([CH2:32][CH2:33][CH2:34][O:35][CH3:36])[C:27]=5[CH:37]=4)[CH2:19][NH:18][CH2:17][CH:16]3[OH:48])=[CH:11][CH:10]=2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 8000Boron trifluoride etherateHCID 68574648HCID 68574648, compound

Product 1

HCID 68575388HCID 68575388, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 139.8 mg of benzyl 4-[4-(5-bromopyrimidin-2-yloxy)phenyl]-3-hydroxy-5-[4 -(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate in 0.5 ml of dichloromethane is added to a mixture of 0.232 ml of boron trifiuoride etherate and 0.4 ml of ethanethiol. The reaction mixture is stirred at room temperature under argon for 20 hours. The solvent is then evaporated off, and 2 ml of water are added to the residue. The aqueous phase is extracted three times with 5 ml of ethyl acetate each time. The combined organic phases are dried with sodium sulphate, filtered and evaporated. The title compound is obtained as a beige wax from the residue by flash chromatography (SiO2 60F).

Workup

  1. customThe solvent is then evaporated off
  2. addition2 ml of water are added to the residue
  3. extractionThe aqueous phase is extracted three times with 5 ml of ethyl acetate each time
  4. dry with materialThe combined organic phases are dried with sodium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-893df30155474e6a8cc39cf51489f9bd
Source dataset
uspto-grants-2010_09
Patent number
US07799779B2

Reaction notes

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