Hexane → HCID 178434316, compound

HRID 2224672Notes

Reaction equation

HRID 2224672 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:9]([OH:16])[CH2:10][NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([S:35](Cl)(=[O:37])=[O:36])[CH:33]=2)[NH:28][N:27]=1.C([O-])(O)=O.[Na+].CCCCCC>ClCCl>[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH:9]([OH:16])[CH2:10][N:11]([CH2:12][CH:13]([CH3:14])[CH3:15])[S:35]([C:32]1[CH:33]=[C:34]2[C:29](=[CH:30][CH:31]=1)[NH:28][N:27]=[C:26]2[CH3:25])(=[O:37])=[O:36])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 8058HexaneHCID 516892Sodium Bicarbonate2×HCID 21878363(1-Benzyl-2-hydroxy-3-isobutylaminopropyl)carbamic acid tert-butyl esterHCID 178434314HCID 178434314, compound

Product 1

HCID 178434316HCID 178434316, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid tert-butyl ester 15 (60 mg, 0.18 mmol) and 3-methyl-1H-indazole-5-sulfonyl chloride (50 mg, 0.22 mmol) in 2 mL dichloromethane was added a 70 ul solution of a saturated NaHCO3 and 30 mg NaHCO3 and stirred overnight. The product was purified by preparative TLC using 1:1 ethyl acetate:hexane to give 95 mg product (99% yield). MS 531 (MH+).

Workup

  1. customThe product was purified by preparative TLC

Sources & evidence

ORD record
ord-9275ef7c5cc64dcd828d4d26016da4d4
Source dataset
uspto-grants-2008_05
Patent number
US07378441B2

Reaction notes

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