L-Glutamic Acid → HCID 86734995, compound

HRID 441623Notes

Reaction equation

HRID 441623 reaction equation
[CH3:1][C@@H:2]1[C@@H:41]([OH:42])[C@@H:40]([CH3:43])[C@H:39]([CH3:44])[O:38][C:36](=[O:37])[CH2:35][C@H:34]([OH:45])[CH2:33][C@H:32]([OH:46])[CH2:31][CH2:30][C@@H:29]([OH:47])[C@H:28]([OH:48])[CH2:27][C@H:26]([OH:49])[CH2:25][C@@:23]2([OH:50])[O:24][C@H:19]([C@H:20]([C:52]([O:54][CH3:55])=[O:53])[C@@H:21]([OH:51])[CH2:22]2)[CH2:18][C@@H:17]([O:56][C@@H:57]2[O:62][C@H:61]([CH3:63])[C@@H:60]([OH:64])[C@H:59]([NH2:65])[C@@H:58]2[OH:66])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=[CH:3]1.[NH2:67][C@H:68]([C:74]([OH:76])=[O:75])[CH2:69][CH2:70][C:71]([OH:73])=[O:72]>O>[CH3:1][C@@H:2]1[C@@H:41]([OH:42])[C@@H:40]([CH3:43])[C@H:39]([CH3:44])[O:38][C:36](=[O:37])[CH2:35][C@H:34]([OH:45])[CH2:33][C@H:32]([OH:46])[CH2:31][CH2:30][C@@H:29]([OH:47])[C@H:28]([OH:48])[CH2:27][C@H:26]([OH:49])[CH2:25][C@@:23]2([OH:50])[O:24][C@H:19]([C@H:20]([C:52]([O:54][CH3:55])=[O:53])[C@@H:21]([OH:51])[CH2:22]2)[CH2:18][C@@H:17]([O:56][C@@H:57]2[O:62][C@H:61]([CH3:63])[C@@H:60]([OH:64])[C@H:59]([NH2:65])[C@@H:58]2[OH:66])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=[CH:3]1.[NH2:67][C@H:68]([C:74]([O-:76])=[O:75])[CH2:69][CH2:70][C:71]([O-:73])=[O:72]

Participants

4

Reactant 2

HCID 33032L-Glutamic AcidHCID 11968030Methylamphotericin B

Product 1

HCID 86734995HCID 86734995, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Amphotericin B methyl ester (9.36 g, 0.01 Mol) is added in portions to a solution of L-glutamic acid (0.81 g, 0.0055 Mol) in 500 ml of water and stirred until complete dissolution (1 hour). The clear solution is then lyopholized. The yield is 88.9%. The product is soluble in water even at concentrations of 10% at RT and when dissolved in water to form a 1% solution is found to have a pH of 6.02.

Sources & evidence

ORD record
ord-15986680fcfc40a4b81d5f45e99b30db
Source dataset
uspto-grants-1977_08
Patent number
US04041232

Reaction notes

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