HCID 86735596, compound → HCID 86735595, compound

HRID 2082687Notes

Reaction equation

HRID 2082687 reaction equation
[CH2:1]([C@@:8]1([O:45][C@H:44]([CH2:46][O:47][C:48]([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)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C@@H:39]([O:40][C:41](=[O:43])[CH3:42])[C@H:12]([O:13][CH2:14][C:15]([NH:17][C@H:18]([C:20]([NH:22][C@@H:23]([C:36](=[O:38])[NH2:37])[CH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[O:21])[CH3:19])=[O:16])[C@@:10]1([NH:67][C:68](=[O:70])[CH3:69])[OH:11])[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C>[CH2:1]([C@@:8]1([O:45][C@H:44]([CH2:46][OH:47])[C@@H:39]([O:40][C:41](=[O:43])[CH3:42])[C@H:12]([O:13][CH2:14][C:15]([NH:17][C@H:18]([C:20]([NH:22][C@@H:23]([C:36](=[O:38])[NH2:37])[CH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[O:21])[CH3:19])=[O:16])[C@@:10]1([NH:67][C:68](=[O:70])[CH3:69])[OH:11])[OH:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([C@@:8]1([O:45][C@H:44]([CH2:46][O:47][C:48]([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:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C@@H:39]([O:40][C:41](=[O:43])[CH3:42])[C@H:12]([O:13][CH2:14][C:15]([NH:17][C@H:18]([C:20]([NH:22][C@@H:23]([C:36](=[O:38])[NH2:37])[CH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[O:21])[CH3:19])=[O:16])[C@@:10]1([NH:67][C:68](=[O:70])[CH3:69])[OH:11])[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86735596HCID 86735596, compound

Product 2

HCID 86735595HCID 86735595, compoundHCID 86735596HCID 86735596, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.94 g of benzyl (benzyl 2-acetamido-4-O-acetyl-6-O-triphenylmethyl-α-D-glucopyranosid-3-O-yl)acetyl-L-alanyl-D-isoglutaminate (12C, n = 2, X1 = L-alanyl, R2 = CH3, R3 = --COCH3) and 10 ml of 70% acetic acid is heated at a 100° C until a clear solution is obtained (about 2 minutes) and heating is contained for a further 2 minutes. The solution is immediately cooled in an ice bath and the precipitate is removed by filtration. The filtrate is evaporated to dryness in vacuo, the residue is triturated with 25 ml ether and the resultant solid is collected by filtration, washed with ether and dried in vacuo giving benzyl (benzyl 2-acetamido-4-O-acetyl-α-D-glucopyranosid-3-O-yl)acetyl-L-alanyl-D-isoglutaminate (12C, n = 2, X1 = L-alanyl, R2 = CH3, R3 = COCH3).

Workup

  1. customis obtained (about 2 minutes)
  2. temperatureheating
  3. temperatureThe solution is immediately cooled in an ice bath
  4. customthe precipitate is removed by filtration
  5. customThe filtrate is evaporated to dryness in vacuo
  6. customthe residue is triturated with 25 ml ether
  7. filtrationthe resultant solid is collected by filtration
  8. washwashed with ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-a5b1bea9391a4ac0a9a1d777671f76b4
Source dataset
uspto-grants-1978_04
Patent number
US04082735

Reaction notes

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