Hydrochloric Acid → HCID 86705513, compound

HRID 2279516Notes

Reaction equation

HRID 2279516 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]([CH3:36])[CH2:34][F:35])=[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.Cl.CC(O)C>C(Cl)Cl>[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]([CH3:36])[CH2:34][F:35])=[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 3776IsopropanolHCID 86705514HCID 86705514, compound

Product 1

HCID 86705513HCID 86705513, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 240 (0.500 g, 0.898 mmol) and DCM (5 mL) at RT was added 6M HCl in IPA (1.50 mL, 8.98 mmol) and the reaction was stirred for 1 h and then concentrated to dryness. The residue was partitioned between aq. Na2CO3 and DCM. The organic fraction was dried, filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a DCM/MeOH gradient (500:30 to 500:35) to afford 0.34 g (85.6%) of I-60 as a mixture of diastereomers: MS m/z (APCI-pos) M+1=442. The racemic mixture was resolved by chiral supercritical fluid chromatography.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was partitioned between aq. Na2CO3 and DCM
  3. customThe organic fraction was dried
  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 500:35)
  8. customto afford 0.34 g (85.6%) of I-60
  9. additionas a mixture of diastereomers

Sources & evidence

ORD record
ord-85827fcebac74cf9a7a0679a34215262
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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