(Diethylamino)sulfur trifluoride → HCID 67076606, compound

HRID 2405206Notes

Reaction equation

HRID 2405206 reaction equation
C[O:2][C:3]([C:5]1([NH:14][C:15](=[O:35])[C:16]2[CH:21]=[CH:20][C:19]([CH:22](O)[CH3:23])=[C:18]([O:25][CH2:26][CH2:27][C:28]3[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=3)[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].C(OC(C1(NC(=O)C2C=CC(C(O)C)=C(OCCC3C=C(C)C=CC=3)C=2)CC2C(=CC=CC=2)C1)=O)C.C(N(S(F)(F)[F:78])CC)C>C(Cl)Cl>[F:78][CH:22]([C:19]1[CH:20]=[CH:21][C:16]([C:15]([NH:14][C:5]2([C:3]([OH:2])=[O:4])[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6]2)=[O:35])=[CH:17][C:18]=1[O:25][CH2:26][CH2:27][C:28]1[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=1)[CH3:23]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 67076463HCID 67076463, compoundHCID 67076600HCID 67076600, compound

Product 1

HCID 67076606HCID 67076606, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of 2-[4-(1-hydroxy-ethyl)-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl ester and 2-[4-(1-hydroxy-ethyl)-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid ethyl ester obtained in example 9 (50 mg) was dissolved in DCM, and diethylaminosulfur trifluoride (33 mg, 0.204 mmol) was added in two portions (second portion after 3.5 h). After complete conversion as detected by HPLC, the mixture was partitioned between EA and a saturated aqueous sodium hydrogencarbonate solution and the aqueous phase extracted with EA. The combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness. The residue was stirred with a HEP/diethyl ether mixture, filtered, and dried in vacuo. The obtained ester was hydrolyzed in analogy to example 2 to give 12 mg of the title compound.

Workup

  1. customthe mixture was partitioned between EA
  2. extractiona saturated aqueous sodium hydrogencarbonate solution and the aqueous phase extracted with EA
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. filtrationfiltered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a4e2404a6de745248275510ca5174df9
Source dataset
uspto-grants-2014_08
Patent number
US08802720B2

Reaction notes

Loading…