Hydrochloric Acid → HCID 69002583, compound

HRID 750059Notes

Reaction equation

HRID 750059 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][C@@H:8]1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:31]=[CH:30][S:29][CH:28]=3)=[CH:23][CH:22]=2)=[CH:16][CH:15]=1.O.[ClH:34]>>[ClH:34].[S:29]1[CH:30]=[CH:31][C:27]([C:24]2[CH:23]=[CH:22][C:21]([CH2:20][C:17]3[CH:18]=[CH:19][C:14]([O:13][CH2:12][C@H:8]4[CH2:9][CH2:10][CH2:11][N:7]4[CH2:6][CH2:5][CH2:4][C:3]([OH:32])=[O:2])=[CH:15][CH:16]=3)=[CH:26][CH:25]=2)=[CH:28]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68997824HCID 68997824, compound

Product 1

HCID 69002583HCID 69002583, compoundYield 75%

Procedure

To a 20 mL vial which contained a solution of the product from step 1 (155 mg, 0.35 mmol) in HCl (4 N in dioxane 4 mL) was added water (0.5 mL) at 0° C. The mixture was allowed to warm to rt and stir at rt for 24 h. The solvent was removed to yield the crude which was purified by recrystallization from THF-ether to afford the title product (125 mg, 75%); LCMS; 100%, APCI+, Calcd: 435.6. Found m/z: 436.5, (M+1). 1H NMR (400 MHz, DMSO-d6); δ 1.74-2.08 (m, 5H), 2.15-2.26 (m, 1H), 2.31-2.40 (m, 2H), 3.05-3.20 (m, 2H), 3.40-3.49 (m, 1H), 3.53-3.63 (m, 1H), 3.83-3.93 (m, 1H), 3.90 (s, 2H), 4.15-4.19 (m, 1H), 4.27 (dd, J1=10.8 Hz, J2=3.6 Hz, 1H), 6.93 (d, J=8.8 Hz, 2H), 7.20 (d, J=8.8 Hz, 2H), 7.23 (d, J=8.4 Hz, 2H), 7.51 (dd, J1=4.8 Hz, J2=1.6 Hz, 1H), 7.60-7.63 (m, 3H), 7.79 (dd, J=2.8 Hz, J2=1.2 Hz, 1H):

Workup

  1. customThe solvent was removed
  2. customto yield the crude which
  3. customwas purified by recrystallization from THF-ether

Sources & evidence

ORD record
ord-9cb33dfa724245e487963a418de03983
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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