Hydrochloric Acid → HCID 76901331, compound

HRID 1478857Notes

Reaction equation

HRID 1478857 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([B:30]2[O:38]C3C(C)(C4CC(C3)C4(C)C)O2)[CH2:14][C:15]2[C:16]([O:28]C)=[C:17]([CH:25]=[CH:26][CH:27]=2)[C:18]([O:20]C(C)(C)C)=[O:19])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].Cl>>[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]2[CH2:14][C:15]3[CH:27]=[CH:26][CH:25]=[C:17]([C:18]([OH:20])=[O:19])[C:16]=3[O:28][B:30]2[OH:38])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86725261HCID 86725261, compound

Product 1

HCID 76901331HCID 76901331, compound

Procedure

tert-Butyl 3-((2R)-2-(2-(3,4-dihydroxyphenyl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoate (200 mg) was mixed with 3 ml of 3N HCl and the reaction mixture was heated at reflux for 1 hr. The reaction solution was cooled and washed with dichloromethane three times. The crude product in the aqueous phase was purified by reverse phase preparative HPLC and dried using lyophilization. ESI-MS m/z 358 (MH)+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 1 hr
  3. temperatureThe reaction solution was cooled
  4. washwashed with dichloromethane three times
  5. customThe crude product in the aqueous phase was purified by reverse phase preparative HPLC
  6. customdried

Sources & evidence

ORD record
ord-0a2815e1aa58411c9fb220a002417720
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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