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Carbamate → HCID 22669293, compound

HRID 1018256
Notes
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Reaction equation

HRID 1018256 reaction equation
[C:1](=[O:4])([O-])[NH2:2].[CH:5]([C:7]1[CH:17]=[CH:16][C:10]([O:11][CH2:12][C:13]([OH:15])=O)=[CH:9][CH:8]=1)=[O:6].[CH3:18][CH2:19][N:20](C(C)C)C(C)C.CN(C(O[N:35]1[N:43]=[N:42][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]1=2)=[N+](C)C)C.[B-](F)(F)(F)F>Cl.O1CCOCC1.C(Cl)Cl.CCOC(C)=O>[N:42]([C:37]1[CH:36]=[CH:41][C:40]([C:1]([NH:2][CH2:18][CH2:19][NH:20][C:13](=[O:15])[CH2:12][O:11][C:10]2[CH:9]=[CH:8][C:7]([CH:5]=[O:6])=[CH:17][CH:16]=2)=[O:4])=[CH:39][CH:38]=1)=[N+:43]=[N-:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 276CarbamateHCID 81531DiisopropylethylamineHCID 89177Acetic acid, 2-(4-formylphenoxy)-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 22669293HCID 22669293, compound

Reagents, catalysts & solvents 3

HCID 6344
Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent
HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

The crude carbamate (0.257 g, 0.84 mmol) was deprotected by stirring in 4N HCl-dioxane (15 mL) for 2 h at room temperature. Volatiles were removed under reduced pressure to give a pinkish solid. 4-Formylphenoxyacetic acid (0.200 g, 1.1 mmol) was dissolved in DCM (3 mL) and DIEA (0.5 mL) was added followed by TBTU (0.350 g, 1,1 mmol) and the amine salt from above (0.240 g, 1 mmol). The mixture was stirred 4 h at room temperature, dissolved in EtOAc and washed sequentially with 5% aqueous K2CO3, KHSO4, water and brine. The extract was dried (MgSO4) and concentrated under reduced pressure to give an off-white solid (0.162 g).

Workup

  1. customVolatiles were removed under reduced pressure
  2. customto give a pinkish solid
  3. washwashed sequentially with 5% aqueous K2CO3, KHSO4, water and brine
  4. dry with materialThe extract was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d741b07c2ea4387b161e80f61bd703b
Source dataset
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06479508B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes