Hydrochloric Acid → HCID 131712097, compound

HRID 126790Notes

Reaction equation

[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][C@H:19]([C:27]([NH:29][C@H:30]([C:35]([O:37][CH3:38])=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[ClH:46].C1(OC)C=CC=CC=1>>[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][C@H:19]([C:27]([NH:29][C@H:30]([C:35]([O:37][CH3:38])=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=[O:28])[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[ClH:46]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 7519Anisole

HCID 12888623HCID 12888623, compound

Product 1

HCID 131712097HCID 131712097, compound

Procedure

As in step A of Example 1A, 2.0 g of Boc-Tyr-DAla-Phe-Met-OCH3 was treated with HCl, anisole, EtOAC to give H-Tyr-DAla-Phe-Met-OCH3.HCl which was dissolved in 40 ml of water, methanol, acetic acid (94:5:1) and applied to a column (2.5×100 cm) of C18Hi+Flosil (80-100 mesh, Applied Science Laboratories, Inc.). The sample was eluted at 3 ml/min with a convex gradient formed from 2 liters of water, methanol, acetic acid (94:5:1) into which was fed methanol, water, acetic acid (50:49:1). The solid resulting from the evaporation of the product peak was dissolved in 10 ml of isopropanol and diluted with 100 ml of hexane to give 1.27 g (68%) of H-Tyr-DAla-Phe-Met-OCH3.HOAc, m.p. 64°-65° C., [α]D26 =10.57°, (c, 1.01 in methanol).

Sources & evidence

ORD record: ord-935518c0bf1942dda0d79b441162c463
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04254024

Reaction notes

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