Water → HCID 86644112, compound

HRID 1091344Notes

Reaction equation

C(N([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)CC(O)=O)(OC(C)(C)C)=O.C1N=CN([C:25]([N:27]2[CH:31]=[N:30][CH:29]=[CH:28]2)=[O:26])C=1.Cl.NC[C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[C:40](=[O:44])[N:39]([CH:45]1[CH2:50][CH2:49][C:48](=[O:51])[NH:47][C:46]1=[O:52])[CH2:38]2.[OH2:53]>CN(C=O)C>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([CH:28]([NH:27][C:25](=[O:26])[O:44][CH2:40][CH2:41][CH2:37][CH3:36])[C:29]([NH:30][CH2:31][C:35]2[CH:36]=[C:37]3[C:41](=[CH:42][CH:43]=2)[C:40](=[O:44])[N:39]([CH:45]2[CH2:50][CH2:49][C:48](=[O:51])[NH:47][C:46]2=[O:52])[CH2:38]3)=[O:53])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of N-Boc-(4′-chlorophenyl) glycine (1.16 g. 4.10 mmol) in DMF (20 mL) was added CDI (0.69 g. 4.30 mmol). The reaction mixture was heated to 40° C. for 2 hrs. 3-(5-Aminomethyl-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione hydrochloride (1.50 g, 4.10 mmol) was then added. After 3.5 hrs at 40° C. water (70 mL) was added. Solid precipitated was isolated by filtration, washed with water (3×20 mL), and dried in vacuo to afford tent-butyl 1-(4-chlorophenyl)-2-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methylamino)-2-oxoethylcarbamate as a white solid (1.77 g, 80% yield). The crude product was used in the next step without further purification.

Workup

customSolid precipitated
customwas isolated by filtration
washwashed with water (3×20 mL)
customdried in vacuo

Sources & evidence

ORD record: ord-169e11adce0841e0a20d67526b85e787
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129375B2

Reaction notes

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