Acetyl chloride → Hydrochloric Acid

HRID 393094Notes

Reaction equation

HRID 393094 reaction equation
C([Cl:4])(=O)C.O1CCCCC1[O:11][C:12]1[CH:13]=[C:14]([CH:46]=[C:47]([O:49]C2CCCCO2)[CH:48]=1)[C:15]([NH:17][CH2:18][C@@H:19]([C:42]([O:44][CH3:45])=[O:43])[NH:20][C:21](=[O:41])[C:22]1[C:27]([Cl:28])=[CH:26][C:25]([C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([OH:39])[CH:34]=2)=[O:30])=[CH:24][C:23]=1[Cl:40])=[O:16]>CO>[ClH:4].[Cl:28][C:27]1[CH:26]=[C:25]([C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([OH:39])[CH:34]=2)=[O:30])[CH:24]=[C:23]([Cl:40])[C:22]=1[C:21]([NH:20][C@H:19]([C:42]([O:44][CH3:45])=[O:43])[CH2:18][NH:17][C:15](=[O:16])[C:14]1[CH:13]=[C:12]([OH:11])[CH:48]=[C:47]([OH:49])[CH:46]=1)=[O:41]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 1317230463-[[3,5-bis[(tetrahydro-2H-pyran-2-yl)oxy]benzoyl]amino]-N-[2,6-dichloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-L-alanine, methyl ester

Product 2

HCID 313Hydrochloric AcidHCID 131723045N-[2,6-dichloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-(3,5-dihydroxybenzoylamino)-L-alanine, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of HCl in methanol was prepared by adding acetyl chloride (10 mL) to methanol at approx. 0° C. The solution was allowed to stir for 10 min and then it was added to 3-[[3,5-bis[(tetrahydro-2H-pyran-2-yl)oxy]benzoyl]amino]-N-[2,6-dichloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-L-alanine, methyl ester (1.60 g, 2.1 mmol). The resulting solution was allowed to stir overnight at room temperature and then the volatiles were evaporated to give N-[2,6-dichloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-(3,5-dihydroxybenzoylamino)-L-alanine, methyl ester (1.26 g, quantitative yield) as an off-white solid.

Workup

  1. stirringto stir overnight at room temperature
  2. customthe volatiles were evaporated

Sources & evidence

ORD record
ord-5845466b3b1143c2a70a67f433850075
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

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