1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68115504, compound

HRID 1503940Notes

Reaction equation

HRID 1503940 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:34])[CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[N:17]=[CH:18][N:19]=[C:20]3[C:27]=2[C:26]2[C@@H:25]([CH2:28][O:29][CH2:30][C:31](O)=[O:32])[CH2:24][CH2:23][C:22]=2[S:21]3)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=[N:41]C=2C=1.CCN=C=NCCCN(C)C.[NH4+].[Cl-]>CN(C)C1C=CN=CC=1.CN(C=O)C>[C:31]([CH2:30][O:29][CH2:28][C@H:25]1[CH2:24][CH2:23][C:22]2[S:21][C:20]3[C:27](=[C:16]([O:15][CH:12]4[CH2:11][CH2:10][CH:9]([N:8]([CH3:34])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])[CH2:14][CH2:13]4)[N:17]=[CH:18][N:19]=3)[C:26]1=2)(=[O:32])[NH2:41]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 86695114HCID 86695114, compound

Product 1

HCID 68115504HCID 68115504, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was added a solution of 2-[[(3S)-12-[(4-[[(tert-butoxy)carbonyl](methyl)amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]methoxy]acetic acid (120 mg, 0.24 mmol, 1.00 equiv), HOBT (49 mg, 0.36 mmol, 1.49 equiv), EDCI (70 mg, 0.37 mmol, 1.50 equiv), 4-dimethylaminopyridine (44 mg, 0.36 mmol, 1.48 equiv) and NH4Cl (76 mg, 1.42 mmol, 5.82 equiv) in distilled DMF (5 mL) at room temperature under nitrogen. The resulting solution was stirred for 14 hrs at ambient temperature, quenched with water and extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (2:1) to afford the desired tert-butyl N-(4-[[(3S)-3-[(carbamoylmethoxy)methyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (75 mg, 63%) as a colorless oil. MS: m/z 491 (M+H)+.

Workup

  1. customTo a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customquenched with water
  4. extractionextracted with 3×50 mL of ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f5040dbc6a7747469160363a751e3cf0
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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