Dicyclohexylcarbodiimide → HCID 71111956, compound

HRID 923617Notes

Reaction equation

HRID 923617 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][C:13]2[CH:50]=[CH:49][C:16]([C:17]([N:19]([CH2:45][C:46]([OH:48])=O)[CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[N:31]=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([C:38]6[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=6)=[CH:34][CH:33]=5)[O:29][N:28]=4)=[CH:23][CH:22]=3)=[O:18])=[CH:15][CH:14]=2)=[O:11])=[C:5]([C:51]([F:54])([F:53])[F:52])[CH:4]=1.[NH2:55][C:56]([CH3:62])([CH3:61])[C:57]([O:59][CH3:60])=[O:58].C1C=CC2N(O)N=NC=2C=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][C:13]2[CH:50]=[CH:49][C:16]([C:17]([N:19]([CH2:45][C:46]([NH:55][C:56]([CH3:62])([CH3:61])[C:57]([O:59][CH3:60])=[O:58])=[O:48])[CH2:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]4[N:31]=[C:30]([C:32]5[CH:33]=[CH:34][C:35]([C:38]6[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=6)=[CH:36][CH:37]=5)[O:29][N:28]=4)=[CH:25][CH:26]=3)=[O:18])=[CH:15][CH:14]=2)=[O:11])=[C:5]([C:51]([F:53])([F:52])[F:54])[CH:4]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 4186341Methyl 2-amino-2-methylpropanoateHCID 711116302-(4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetic acid

Product 1

HCID 71111956HCID 71111956, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 2-(4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetic acid 354 (15 mg, 0.02 mmol), methyl 2-amino-2-methylpropanoate (3.6 mg, 0.03 mmol) and HOBt (3.03 mg, 0.02 mmol) in anhydrous DMF (0.5 mL) was added dicyclohexyl carbodiimide (DCC) (4.6 mg, 0.02 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and allowed stir at room temperature for 36 h. The reaction was quenched with saturated NaHCO3 (2 mL) then extracted with EA (2×3 mL). The combined organic extract was washed with brine (5 mL), dried (MgSO4), filtered and concentrated to afford methyl 2-(2-(4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetamido)-2-methylpropanoate INT-72 which was used in the next step without purification. LCMS-ESI (m/z) calculated for C46H42F3N5O7: 834; no ion observed, tR=4.44 min (Method 3).

Workup

  1. stirringallowed stir at room temperature for 36 h
  2. customThe reaction was quenched with saturated NaHCO3 (2 mL)
  3. extractionthen extracted with EA (2×3 mL)
  4. extractionThe combined organic extract
  5. washwas washed with brine (5 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-eca3e1f57da24ad9a190bd0f863dd65b
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

Loading…