tert-Butyl Formate → HCID 57656138, compound

HRID 2041111Notes

Reaction equation

HRID 2041111 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[OH:19].[C:20]([O:24][C:25]([NH:27][CH2:28][CH2:29]O)=[O:26])([CH3:23])([CH3:22])[CH3:21].C(OC(C)(C)C)=O>CCCCCC.CCOC(C)=O>[C:20]([O:24][C:25]([NH:27][CH2:28][CH2:29][O:19][C:3]1[C:4]2[CH2:10][CH2:9][N:8]([C:11](=[O:16])[C:12]([F:15])([F:13])[F:14])[CH2:7][CH2:6][C:5]=2[CH:17]=[CH:18][C:2]=1[Cl:1])=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 61207tert-Butyl FormateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 58757109HCID 58757109, compound

Product 1

HCID 57656138HCID 57656138, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Use a method similar to the General Procedure 4-3, using 7-chloro-6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (277 mg, 0.94 mmol) and N-(tert-butoxycarbonyl)ethanolamine (244 mg, 1.51 mmol) to give, after chromatography on silica gel eluting with hexane/EtOAc (1:0 and 3:1), the desired intermediate (392 mg, 95%). MS (ES+) m/z: 337 (M+H-Boc)+.

Workup

  1. customto give

Sources & evidence

ORD record
ord-c8d86e264d4548f0a9bb9e6b1d96fa71
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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