N-BOC-ethylenediamine → HCID 86725278, compound

HRID 1478882Notes

Reaction equation

HRID 1478882 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C@H:12]([B:29]1[O:37][CH:36]2[C:31]([CH3:41])([CH:32]3[CH2:38][CH:34]([CH2:35]2)[C:33]3([CH3:40])[CH3:39])[O:30]1)[CH2:13][C:14]1[C:15]([O:27][CH3:28])=[C:16]([CH:24]=[CH:25][CH:26]=1)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[NH2:42][CH2:43][CH2:44][NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49]>CO>[C:48]([O:47][C:46]([NH:45][CH2:44][CH2:43][NH:42][C:2]([C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:4]([NH:3][C@H:12]([B:29]1[O:37][CH:36]2[C:31]([CH3:41])([CH:32]3[CH2:38][CH:34]([CH2:35]2)[C:33]3([CH3:39])[CH3:40])[O:30]1)[CH2:13][C:14]1[C:15]([O:27][CH3:28])=[C:16]([CH:24]=[CH:25][CH:26]=1)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:11])=[O:1])=[O:52])([CH3:51])([CH3:50])[CH3:49]

Participants

4

Reactant 2

HCID 187201N-BOC-ethylenediamineHCID 86725279HCID 86725279, compound

Product 1

HCID 86725278HCID 86725278, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To tert-butyl 3-((2R)-2-(1,3-dioxoisoindolin-2-yl)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoate (100 mg from Step 1, Example 53) in 2 mL methanol was added tert-butyl 2-aminoethylcarbamate (1.1 eq). The resulting reaction mixture was stirred at reflux for 2 hr. Methanol was then removed under reduced pressure. The crude product was used in the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. temperatureat reflux for 2 hr
  3. customMethanol was then removed under reduced pressure
  4. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-bc96cc7f026c4c99956aa3c72e24db4c
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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