Carbamate → HCID 22669293, compound

HRID 2117004Notes

Reaction equation

HRID 2117004 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-0c14e45ea2ed416b9b0bdded8b4b7d95
Source dataset
uspto-grants-2008_10
Patent number
US07439258B2

Reaction notes

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