4-Methylmorpholine → HCID 68158150, compound

HRID 242781Notes

Reaction equation

HRID 242781 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH3:16])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[NH2:37])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[NH:37][C:13](=[O:15])[C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH3:16])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 736104N-carbobenzyloxyalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11380765tert-Butyl 4-(2-aminophenylamino)piperidine-1-carboxylate

Product 1

HCID 68158150HCID 68158150, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of (S)-2-benzyloxycarbonylaminopropionic acid (230 mg, 1.03 mmol), 4-(2-aminophenylamino)piperidine-1-carboxylic acid tertbutyl ester (200 mg, 0.686 mmol), HOBt (102 mg, 0.755 mmol), 4-methylmorpholine (166 μL, 1.51 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (197 mg, 1.03 mmol) in DCM (7 mL) was stirred at RT for 3 h. The reaction mixture was then diluted with additional DCM and the organic layer was washed with water, then dried and concentrated in vacuo affording 4-[2-((S)-2-benzyloxycarbonylaminopropionylamino)phenylamino]piperidine-1-carboxylic acid tertbutyl ester as a purple/brown oil (436 mg, quantitative). LCMS: RT 3.66 min [M+H]+ 497.2.

Workup

  1. washthe organic layer was washed with water
  2. customdried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e636978f3a8447480c6ab038884dd8c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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