Hydrochloric Acid → HCID 49837193, compound

HRID 2206317Notes

Reaction equation

HRID 2206317 reaction equation
[C:1]1([CH2:7][S:8]([NH:11][C@H:12]([B:20]([O:22]C23CC(C2(C)C)CCC3(O)C)[OH:21])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C1(B(O)O)C=CC=CC=1.C1(B(O)O)C=CC=CC=1.C12(O)CC(C1(C)C)CCC2(O)C>CC#N.CCCCCC>[C:1]1([CH2:7][S:8]([NH:11][C@H:12]([B:20]([OH:22])[OH:21])[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 66827Phenylboronic AcidHCID 131735850HCID 131735850, compoundHCID 131735854HCID 131735854, compound

Product 1

HCID 49837193HCID 49837193, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8058HexaneSolvent2×

Procedure

To a solution of 15a (245 mg, 0.54 mmol) in CH3CN (3 mL), HCl (1M aqueous solution, 350 μL, 0.35 mmol), phenylboronic acid (62 mg, 0.51 mmol) and n-hexane (3 mL) were sequentially added and the resulting biphasic solution was vigorously stirred. After 30 min the n-hexane layer, containing the pinanediol phenylboronate, was removed and fresh n-hexane (3 mL) was added. This last procedure was repeated several times until a TLC analysis revealed no remaining pinanediol boronate. The acetonitrile phase was then concentrated affording 16 as a yellowish solid (159 mg, 92% yield). Mp 107° C. (dec). [α]D+78.0 (c 1.0, MeOH). 1H-NMR (400 MHz, MeOD): δ 2.83 (2H, d, J 7.1, CHCH2), 3.05 (1H, t, J 7.1, BCH), 4.20 (2H, s, CH2SO2), 7.16-7.44 (10H, m, HArom). 13C-NMR (100 MHz, MeOD): δ 38.8, 39.3 (CB), 58.6, 126.1, 127.2, 128.0, 128.2, 129.0, 130.1, 130.6, 133.3. EI-MS and elemental analysis were not obtainable, but exposure of 16 to an equimolar amount of (+)-pinanediol in anhydrous THF afforded compound 15a in quantitative yield and satisfactory elemental analysis; Anal. Calcd. for C25H32BNO4S: C, 66.23; H, 7.11; N, 3.09; S, 7.07. Found: C, 66.14; H, 6.91; N, 3.32; S, 6.89.

Workup

  1. customwas removed
  2. additionfresh n-hexane (3 mL) was added
  3. concentrationThe acetonitrile phase was then concentrated

Sources & evidence

ORD record
ord-a329366c42284e9f941b999602f16c23
Source dataset
uspto-grants-2016_06
Patent number
US09371337B2

Reaction notes

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