Carbamate → HCID 22669293, compound

HRID 1280080Notes

Reaction equation

HRID 1280080 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]

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 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 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-72d7a7c6175c4f3dbc1c1851388a2b54
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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