L-Tyrosine 1,1-dimethylethyl ester → HCID 68174317, compound

HRID 1479926Notes

Reaction equation

HRID 1479926 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.C(OC(=O)[C@H](CC1C=CC(O)=CC=1)N)(C)(C)C>>[F:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6950582L-Tyrosine 1,1-dimethylethyl esterHCID 59054573HCID 59054573, compound

Product 1

HCID 68174317HCID 68174317, compound

Procedure

Following 18a synthetic method, using B2 (118.65 mg, 0.5 mmol) instead of A2 gave 18b as a colorless oil; (56.33 mg, 49.8%). [α]D25: −14.4 (c=0.27, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 8.20 (s, 1H), 7.56-7.48 (m, 2H), 7.44-7.35 (m, 2H), 7.03-6.95 (m, 3H), 6.70-6.65 (m, 2H), 4.18-4.11 (m, 1H), 3.06-2.81 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.53, 163.77, 160.48, 156.28, 143.54, 131.00, 130.36, 126.92, 122.75, 119.25, 115.07, 113.89, 113.57, 57.63, 37.74; HRMS (ESI): calcd for: C15H14FNO5S [M+Na]+=362.0469, obsd [M+Na]+=362.0485.

Sources & evidence

ORD record
ord-54a46631ef474ae89911f2bced7d13a0
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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