Methanol → HCID 131711064, compound

HRID 2082688Notes

Reaction equation

HRID 2082688 reaction equation
[CH2:1]([C@@:8]1([O:41][C@H:40]([CH2:42][OH:43])[C@@H:38]([OH:39])[C@H:11]([O:12][CH2:13][C:14]([NH:16][C@H:17]([C:19]([NH:21][C@@H:22]([C:35](=[O:37])[NH2:36])[CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])=[O:20])[CH3:18])=[O:15])[C@H:10]1[NH:44][C:45](=[O:47])[CH3:46])[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:48](OC(=O)C)(=[O:50])[CH3:49].CO>N1C=CC=CC=1>[CH2:1]([C@@:8]1([O:41][C@H:40]([CH2:42][O:43][C:48](=[O:50])[CH3:49])[C@@H:38]([OH:39])[C@H:11]([O:12][CH2:13][C:14]([NH:16][C@H:17]([C:19]([NH:21][C@@H:22]([C:35](=[O:37])[NH2:36])[CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])=[O:20])[CH3:18])=[O:15])[C@H:10]1[NH:44][C:45](=[O:47])[CH3:46])[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 86735594HCID 86735594, compound

Product 1

HCID 131711064HCID 131711064, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 0.33 g of benzyl (benzyl 2-acetamido-2-deoxy-α-D-glucopyranosid-3-O-yl)acetyl-L-alanyl-D-isoglutaminate (12A, n = 2, X1 = L-alanyl, R2 = CH3) in 5 ml of pyridine is stirred at 0° whilst a solution of 0.095 ml of acetic anhydride in 1 ml of pyridine is added dropwise over 30 minutes. The resultant solution is stored at 0° C for 16 hours at which time 1 ml of methanol is added and the mixture is evaporated to dryness. The residue thus obtained is partitioned between 100 ml of chloroform and 100 ml of water, the chloroform phase is dried over magnesium sulfate and concentrated in vacuo, giving 0.36 g of crude product which is purified by preparative thick-layer chromatography giving benzyl (benzyl 2-acetamido-6-O-acetyl-2-deoxy-α-D-glucopyranosid-3-O-yl)acetyl-L-alanyl-D-isoglutamine (12F, n = 2, X1 =L-alanyl, R2 = CH3, R3 = --COCH3).

Workup

  1. additionis added dropwise over 30 minutes
  2. additionis added
  3. customthe mixture is evaporated to dryness
  4. customThe residue thus obtained
  5. customis partitioned between 100 ml of chloroform and 100 ml of water
  6. dry with materialthe chloroform phase is dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customgiving 0.36 g of crude product which
  9. customis purified by preparative thick-layer chromatography

Sources & evidence

ORD record
ord-b8c38aa9312b46bb97ddfcdba6dd0885
Source dataset
uspto-grants-1978_04
Patent number
US04082735

Reaction notes

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