HCID 1549462, compound → HCID 66756032, compound

HRID 222397Notes

Reaction equation

[CH:1]1[CH:6]=[C:5]2[C:7]([CH2:10][C@@H:11]([NH:15][C:16]([CH2:18][CH2:19][C@@H:20]([NH2:24])[C:21](O)=[O:22])=[O:17])[C:12]([OH:14])=[O:13])=[CH:8][NH:9][C:4]2=[CH:3][CH:2]=1.[NH2:25][C@@H](C(N[C@@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1)=O)CCC(=O)O>>[NH2:24][C@@H:20]([C:21](=[O:22])[NH2:25])[CH2:19][CH2:18][C:16]([NH:15][C@@H:11]([C:12]([OH:14])=[O:13])[CH2:10][C:7]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[NH:9][CH:8]=1)=[O:17]

Participants

Reactant 2

HCID 1549462HCID 1549462, compound

HCID 7275810Thymodepressin2×

Product 1

HCID 66756032HCID 66756032, compound

Procedure

A method for the preparation of thymodepressin was disclosed in example 1 of U.S. Pat. Nos. 5,736,519, 6,103,699 and 6,410,515. However, the manufacture of thymodepressin on a large scale cannot be conducted using the experimental details of this method since a mixture of D-glutamyl-D-tryptophan and D-isoglutamyl-D-tryptophan is produced which must be separated and purified by ion exchange chromatography resulting in a very low yield (12.25%) of thymodepressin.

Sources & evidence

ORD record: ord-c83caf53888145289d99032bc3e7b343
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207217B2

Reaction notes

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