1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67057865, compound

HRID 2361705Notes

Reaction equation

HRID 2361705 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH:14]([C:18]([OH:20])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[OH:43][CH:44]1[CH2:47][NH:46][CH2:45]1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[OH:43][CH:44]1[CH2:47][N:46]([C:18]([CH:14]2[CH2:15][CH2:16][CH2:17][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:12][CH2:13]2)=[O:20])[CH2:45]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 66833473HCID 66833473, compound

Product 1

HCID 67057865HCID 67057865, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-[(benzyloxy)carbonyl]azepane-4-carboxylic acid (317 mg, 1.14 mmol) in DMF (5 ml) was added HOBt (154 mg, 1.14 mmol) followed by EDCI (218 mg, 1.14 mmol). After 5 minutes, a solution of 3-hydroxyazetidine hydrochloride (138 mg, 1.26 mmol) and DIPEA (0.44 ml, 2.51 mmol) in DMF (1 ml) was added and the resulting solution was stirred for 12 hours at room temperature. The mixture was diluted with EtOAc (30 ml) and washed with saturated aqueous NaHCO3 (3×15 ml), dried (MgSO4), filtered and concentrated. The residue was purified by silica FCC (using a gradient of eluents; 99:1 to 92:8 DCM/MeOH) to give the title product as colourless oil (265 mg, 70%).

Workup

  1. washwashed with saturated aqueous NaHCO3 (3×15 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica FCC (

Sources & evidence

ORD record
ord-4588b49296414a3db50e619b44f482b7
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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