1-Hydroxybenzotriazole → HCID 86654321, compound

HRID 1886984Notes

Reaction equation

HRID 1886984 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]=1[S:16][C@@H:17]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C@@H:18]([OH:22])[C:19](O)=[O:20].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(OCC)(=O)C.CO>CN(C=O)C>[CH2:9]([O:8][C:4]1[C:3]2[S:16][C@@H:17]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[C@@H:18]([OH:22])[C:19](=[O:20])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21584119Ethylacetate methanolHCID 86654320HCID 86654320, compound

Product 1

HCID 86654321HCID 86654321, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 2.11 g (4.96 mmol) of (+/−)-(2S,3S)-3-(2-amino-6-(benzyloxy)phenylthio)-2-hydroxy-3-(4-methoxyphenyl)propanoic acid in 25 mL of DMF was added 1.24 g (6.47 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 871 mg (6.45 mmol) of 1-hydroxybenzotriazole. The solution was stirred at 22° C. for 16 hours, and a solution of 7:3 ethyl acetate/methanol was added to the reaction. The organic layer was washed with 1 N HCl (2×) and then with a 1:1 mixture of satd. NaHCO3 and brine (2×). The organic layer was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography on silica gel, eluting first with hexane then gradually increasing to 40% ethyl acetate/hexane to give (+/−)-(2S,3S)-9-(benzyloxy)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one.

Workup

  1. washThe organic layer was washed with 1 N HCl (2×)
  2. additionwith a 1:1 mixture of satd
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting first with hexane
  7. temperaturethen gradually increasing to 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-94651a24740d4386a90b0a9bc882dcf3
Source dataset
uspto-grants-2013_08
Patent number
US08501727B2

Reaction notes

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