Hydrochloric Acid → HCID 86705475, compound

HRID 2279454Notes

Reaction equation

HRID 2279454 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([NH:19][C:20]([N:22]1[CH2:31][CH2:30][C:29]2[CH:28]=[N:27][C:26]([NH:32][CH:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[N:25][C:24]=2[CH2:23]1)=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=1)(C(C)(C)C)(C)C.C(Cl)Cl.Cl>CC(O)C>[Cl:18][C:13]1[CH:12]=[C:11]([C@H:10]([NH:19][C:20]([N:22]2[CH2:31][CH2:30][C:29]3[CH:28]=[N:27][C:26]([NH:32][CH:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[N:25][C:24]=3[CH2:23]2)=[O:21])[CH2:9][OH:8])[CH:16]=[CH:15][C:14]=1[Cl:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 86705476HCID 86705476, compound

Product 1

HCID 86705475HCID 86705475, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 69a (0.175 g, 0.301 mmol) and DCM (3 mL) was added 6M HCl (0.0110 g, 0.301 mmol) in IPA and the reaction was stirred for 2 h and then poured into satd. aq. Na2CO3 and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a DCM/MeOH gradient (500:30 to 500:45) to afford 0.030 g (21.3%) of I-43: MS m/z (APCI-pos) M+1=466.

Workup

  1. additionpoured into satd
  2. extractionaq. Na2CO3 and extracted with DCM
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with a DCM/MeOH gradient (500:30 to 500:45)
  8. customto afford 0.030 g (21.3%) of I-43

Sources & evidence

ORD record
ord-d565fb0071e1409d9e277a87e8bf3973
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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