Hydrochloric Acid → HCID 22619721, compound

HRID 841147Notes

Reaction equation

HRID 841147 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:25][C:26]1[N:30]([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:29]=[N:28][CH:27]=1)[C:13]([CH:15]([NH:20][CH2:21]/[CH:22]=[CH:23]/[CH3:24])[C:16]([O:18]C)=[O:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.[OH-].[Na+].Cl>CO.CCOC(C)=O.C1COCC1>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:25][C:26]1[N:30]([C:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:29]=[N:28][CH:27]=1)[C:13]([CH:15]([NH:20][CH2:21]/[CH:22]=[CH:23]/[CH3:24])[C:16]([OH:18])=[O:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 22619729HCID 22619729, compound

Product 1

HCID 22619721HCID 22619721, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

A solution of methyl 2-[2-[(benzyloxy)carbonyl]amino-3-(1-trityl-1H-5-imidazolyl)propanoyl][(E)-2-butenyl]aminoacetate (2.23 g, 3.4 mmol) in MeOH (20 mL )/dioxane (15 mL) was treated with 2 N NaOH (7.0 mL, 14.0 mmol) and stirred at room temperature for 0.5 hour. After adding 2 N HCl (7.0 mL, 14.0 mmol), the mixture was stripped to a solid. This was mixed with EtOAc/THF and filtered to remove NaCl. Removal of the solvent under reduced pressured left 2.06 g (94.5% yield) of the product as a white solid foam. MS, rn/z 643 (M+H+).

Workup

  1. filtrationfiltered
  2. customto remove NaCl
  3. customRemoval of the solvent under reduced pressured

Sources & evidence

ORD record
ord-dabd7a15da424259a5382c711770257e
Source dataset
uspto-grants-2002_04
Patent number
US06369034B1

Reaction notes

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