Sodium Bicarbonate → HCID 178427584, compound

HRID 1106952Notes

Reaction equation

HRID 1106952 reaction equation
[NH:1]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C@H:2]([C:28]([OH:30])=[O:29])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:27])[NH:8][S:9]([C:12]1[C:25]([CH3:26])=[C:23]([CH3:24])[C:22]2[O:21][C:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][C:15]=2[C:13]=1[CH3:14])(=[O:11])=[O:10].C([O-])(O)=O.[Na+]>ClC(Cl)C>[NH:1]([C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[C@H:2]([C:28]([O:30][C:13]([CH3:15])([CH3:14])[CH3:12])=[O:29])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:27])[NH:8][S:9]([C:12]1[C:25]([CH3:26])=[C:23]([CH3:24])[C:22]2[O:21][C:18]([CH3:19])([CH3:20])[CH2:17][CH2:16][C:15]=2[C:13]=1[CH3:14])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178427583HCID 178427583, compound

Product 1

HCID 178427584HCID 178427584, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

A] A slurry of 6.9 g (12 mmoles) of Z-Arg(Pmc)-OH in 60 ml of dichloroethane was added with 8.64 ml (36 mmoles) of N,N-dimethylformamide-di-tert.-butylacetale, in 60 minutes at 50° C. At the end of the addition, the reaction mixture was kept under stirring for 40 minutes at 50° C., then it was added with 20 ml of an aqueous solution of 5% sodium hydrocarbonate. The dichloroethane was evaporated under vacuum and the aqueous phase was diluted with 100 ml of ethyl acetate. The organic phase was separated and washed with an aqueous solution of 5% sodium hydrocarbonate and with a saturated aqueous solution of sodium chloride till neutrality. The organic phase was then anhydrified and evaporated under vacuum, and the resulting crude was purified on a silica gel column (eluent: ethyl acetate/n-hexane 6:4). There were obtained 3.4 g of Z-Arg(Pmc)-OtBu (HPLC, gradient (I): R.t. 32 min.; purity 99%).

Workup

  1. additionAt the end of the addition
  2. customThe dichloroethane was evaporated under vacuum
  3. additionthe aqueous phase was diluted with 100 ml of ethyl acetate
  4. customThe organic phase was separated
  5. washwashed with an aqueous solution of 5% sodium hydrocarbonate and with a saturated aqueous solution of sodium chloride till neutrality
  6. customevaporated under vacuum
  7. customthe resulting crude was purified on a silica gel column (eluent: ethyl acetate/n-hexane 6:4)

Sources & evidence

ORD record
ord-34c7866207734cbd91dddbb277b2acae
Source dataset
uspto-grants-2000_05
Patent number
US06057295

Reaction notes

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