Trityl chloride → HCID 86735593, compound

HRID 2082686Notes

Reaction equation

HRID 2082686 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]1([C:54](Cl)([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>N1C=CC=CC=1>[CH2:1]([C@@:8]1([O:41][C@H:40]([CH2:42][O:43][C:54]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[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

4

Reactant 2

HCID 6456Trityl chlorideHCID 86735594HCID 86735594, compound

Product 1

HCID 86735593HCID 86735593, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 0.66 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) and 0.56 g of triphenylmethyl chloride in 10 ml of pyridine is stirred at 22° C for 5 days and is then evaporated to dryness in vacuo. The residue is partitioned between 30 ml of chloroform and 30 ml of water, the chloroform phase is extracted twice more with 30 ml of water, dried over magnesium sulfate, concentrated in vacuo and the residue is triturated with 50 ml of ether. The resulting solid is collected by filtration, washed with ether and dried giving 0.74 g of benzyl (benzyl 2-acetamido-2-deoxy-6-O-triphenylmethyl-α-D-glucopyranosid-3-O-yl)acetyl-L-alanyl-D-isoglutaminate (12B, n = 2, X1 = L-alanyl, R2 = CH3).

Workup

  1. customis then evaporated to dryness in vacuo
  2. customThe residue is partitioned between 30 ml of chloroform and 30 ml of water
  3. extractionthe chloroform phase is extracted twice more with 30 ml of water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe residue is triturated with 50 ml of ether
  7. filtrationThe resulting solid is collected by filtration
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-6549b82f54a34f71b687417e41c7f6d6
Source dataset
uspto-grants-1978_04
Patent number
US04082735

Reaction notes

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