1,2-Dichloroethane → HCID 86690060, compound

HRID 539409Notes

Reaction equation

HRID 539409 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)(=[O:22])=[O:21])([C:17](O)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:36](Cl)[CH2:37]Cl.C1C=CC2[N:48]([OH:49])N=NC=2C=1.C(N([CH2:55][CH3:56])CC)C.CN([CH:60]=[O:61])C>>[O:29]([C:26]1[CH:25]=[CH:24][C:23]([S:20]([C:14]2([C:17](=[O:18])[NH:48][O:49][CH:37]3[CH2:36][CH2:56][CH2:55][CH2:60][O:61]3)[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH2:16][CH2:15]2)(=[O:22])=[O:21])=[CH:28][CH:27]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 86690059HCID 86690059, compound

Product 1

HCID 86690060HCID 86690060, compound

Procedure

Benzyl 4-((4-phenoxyphenyl)sulfonyl)-4-(((tetrahydro-2H-pyran-2-yl)oxy)carbamoyl)piperidine-1-carboxylate was synthesized as shown in FIG. 12. A 200 ml RBF equipped with magnetic stir bar was charged with 1.48 g (2.99 mmole) 1-((benzyloxy)carbonyl)-4-((4-phenoxyphenyl)sulfonyl)piperidine-4-carboxylic acid, 0.49 g (4.18 mmole) OTHP-hydroxylamine, 0.8 g (4.18 mmole) EDC, 0.64 g (4.18 mmole) HOBt, and 1.25 ml (8.96 mmole) triethylamine in 30 ml DMF. The reaction mixture was stirred at room temperature overnight. The reaction was concentrated in vacuo and partitioned between EA and satd. aq. sodium bicarbonate. The organics were washed with 10% aq. Citric acid, brine, dried, and concentrated in vacuo. This material was vacuum dried overnight to afford 1.50 g (85%) of dry white foam. The sample analyzed by direct infusion MS, which indicated >90% product with some trace impurities. HRMS(theoretical) M+H=595.2108 g/mol. HRMS(observed) M+H=595.2109 g/mol.

Workup

  1. customA 200 ml RBF equipped with magnetic stir bar
  2. concentrationThe reaction was concentrated in vacuo
  3. custompartitioned between EA
  4. washThe organics were washed with 10% aq. Citric acid, brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customdried overnight

Sources & evidence

ORD record
ord-cf5cb6a688ea437db74753d6f5211c9f
Source dataset
uspto-grants-2014_10
Patent number
US08871189B2

Reaction notes

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