Thioglycolic Acid → HCID 13146043, compound

HRID 851152Notes

Reaction equation

HRID 851152 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:11]([NH:13][C@@H:14]([C:20]([NH:22][CH2:23][C:24]([N:26]([CH2:44][CH3:45])[C@H:27]([C:35]([NH:37][NH:38][C:39]([CH2:41][CH2:42][CH3:43])=[O:40])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:25])=[O:21])[CH2:15][CH2:16][S:17]([CH3:19])=[O:18])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(O)(=O)CS.N[C@H](C(O)=O)CCSC.N[C@H](C(O)=O)CC1C=CC(O)=CC=1>CO>[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:20]([NH:22][CH2:23][C:24]([N:26]([CH2:44][CH3:45])[C@H:27]([C:35]([NH:37][NH:38][C:39]([CH2:41][CH2:42][CH3:43])=[O:40])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:25])=[O:21])[CH2:15][CH2:16][S:17]([CH3:19])=[O:18])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 6057L-TyrosineHCID 6137L-Methionine2×HCID 13146041HCID 13146041, compound

Product 1

HCID 13146043HCID 13146043, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

By the same procedure as in Example 2-(IV), there was obtained the objective compound from 0.50 g of BOC-Tyr-(D)-Met(O)-Gly-EtPhe-NHNHCOCH2CH2CH3. Yield: 0.29 g, [α]D24 +17.6° (c=0.52, MeOH), Rf2 0.26. Amino acid analysis (4% thioglycolic acid/6 N hydrochloric acid hydrolysis): Gly 1.00(1), Met 1.03(1), Tyr 0.98(1).

Sources & evidence

ORD record
ord-60ccab99caf049e392f60d471a72e980
Source dataset
uspto-grants-1983_05
Patent number
US04382923

Reaction notes

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