1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86695172, compound

HRID 1504018Notes

Reaction equation

HRID 1504018 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[C:17]3[C:18]4[CH2:19][C@@H:20]([CH2:29][C:30]([OH:32])=O)[CH2:21][CH2:22][C:23]=4[S:24][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-].CC[N:37]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CN(C)C1C=CN=CC=1>[C:30]([CH2:29][C@@H:20]1[CH2:19][C:18]2[C:17]3[C:16]([O:15][CH:12]4[CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:14][CH2:13]4)=[N:28][CH:27]=[N:26][C:25]=3[S:24][C:23]=2[CH2:22][CH2:21]1)(=[O:32])[NH2:37]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 86695170HCID 86695170, compound

Product 1

HCID 86695172HCID 86695172, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(12S)-3-[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)oxy]-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]acetic acid (148 mg, 0.32 mmol, 1.00 equiv) in 6 mL of distilled DMF was added NH4Cl (103 mg, 1.93 mmol, 6.00 equiv), EDCI (92 mg, 0.48 mmol, 1.50 equiv), 4-dimethylaminopyridine (58 mg, 0.47 mmol, 1.50 equiv) and HOBt (65 mg, 0.48 mmol, 1.50 equiv) successively and the resulting solution was stirred overnight at room temperature. The reaction was then quenched with water and extracted with 3×50 mL of ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (2:1) to give 80 mg (54%) of the desired tert-butyl N-(4-[[(12S)-12-(carbamoylmethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate as a white solid. MS: m/z 460 (M+H)+.

Workup

  1. customThe reaction was then quenched with water
  2. extractionextracted with 3×50 mL of ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2d83f9a972b04d64a8b97df9ff860a2d
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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