Sodium Sulfate → HCID 73063680, compound

HRID 1767027Notes

Reaction equation

HRID 1767027 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.Cl.[CH2:15]([O:22][CH2:23][C:24]([C:27]1[S:31][C:30]([NH:32][C:33](=[O:39])[CH:34]([NH2:38])[CH2:35][CH2:36][CH3:37])=[N:29][N:28]=1)([CH3:26])[CH3:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C.C(N(CC)CC)C>[CH2:15]([O:22][CH2:23][C:24]([C:27]1[S:31][C:30]([NH:32][C:33](=[O:39])[CH:34]([NH:38][CH:7]2[CH2:6][CH2:5][C:4]3[C:9](=[C:10]([F:12])[CH:11]=[C:2]([F:1])[CH:3]=3)[CH2:8]2)[CH2:35][CH2:36][CH3:37])=[N:29][N:28]=1)([CH3:25])[CH3:26])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 24436Sodium SulfateHCID 40764316,8-Difluoro-2-tetraloneHCID 5049666Sodium triacetoxyborohydrideHCID 1317264962-amino-pentanoic acid [5-(2-benzyloxy-1,1-dimethyl-ethyl)-[1,3,4]thiadiazol-2-yl]-amide HCl

Product 1

HCID 73063680HCID 73063680, compoundYield 38.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 6,8-difluoro-3,4-dihydro-1H-naphthalen-2-one (521 mg, 2.86 mmol), 2-amino-pentanoic acid [5-(2-benzyloxy-1,1-dimethyl-ethyl)-[1,3,4]thiadiazol-2-yl]-amide HCl (1140 mg, 2.86 mmol) in methylene chloride (25 mL) was treated with triethyl amine (0.4 mL), then acetic acid (0.7 mL) and sodium sulfate. After stirring for 15 min, 95% pure sodium triacetoxy borohydride (767 mg, 3.4 mmol) was added and the resulting mixture was stirred at rt overnight. The mixture was quenched with dilute water, acidified to pH 3, extracted twice with methylene chloride. The orgainic layer was washed with dilute sodium hydroxide to pH 7, separated, dried and concentrated to give a dark brown oil. The oil was purified by silica gel column chromatography using 1% methanol in methylene chloride as eluent to give 2-(6,8-difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(2-benzyloxy-1,1-dimethyl-ethyl)-[1,3,4]thiadiazol-2-yl]-amide (578 mg) as a brown oil, LC-MS, RT=2.6 min, M+1=529.1. The corresponding HCl salt was prepared as a light pink solid after triturating with hexane.

Workup

  1. stirringthe resulting mixture was stirred at rt overnight
  2. customThe mixture was quenched with dilute water
  3. extractionextracted twice with methylene chloride
  4. washThe orgainic layer was washed with dilute sodium hydroxide to pH 7
  5. customseparated
  6. customdried
  7. concentrationconcentrated
  8. customto give a dark brown oil
  9. customThe oil was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4822b7b1e6024976b51963cf15a3767c
Source dataset
uspto-grants-2007_06
Patent number
US07232820B2

Reaction notes

Loading…