L-Tyrosine 1,1-dimethylethyl ester → HCID 40492103, compound

HRID 1479928Notes

Reaction equation

HRID 1479928 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C:13]([OH:15])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(OC(=O)[C@H](CC1C=CC(O)=CC=1)N)(C)(C)C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)[C:13]([OH:15])=[O:14])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6950582L-Tyrosine 1,1-dimethylethyl esterHCID 59054458HCID 59054458, compound

Product 1

HCID 40492103HCID 40492103, compound

Procedure

Following 19a synthetic method, using B2 (118.65 mg, 0.5 mmol) instead of A2 gave 19b as a colorless oil; (96.03 mg, 56.6%). [α]D25: −13.7 (c=0.23, CHCl3); 1H-NMR (300 MHz, CDCl3): δ 7.78-7.71 (m, 2H), 7.26-7.17 (m, 7H), 6.92 (d, J=9 Hz, 1H), 4.25-4.13 (m, 1H), 3.15-2.90 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.56, 166.28, 162.95, 137.52, 136.53, 129.74, 129.62, 129.39, 128.24, 126.68, 115.94, 115.63, 57.31, 38.48; HRMS (ESI): calcd for: C15H14FNO4S [M+Na]+=346.0520, obsd [M+Na]+=346.0523.

Sources & evidence

ORD record
ord-be3622835ff447c6abaac38a8776bac6
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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