L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → HCID 13578785, compound

HRID 980235Notes

Reaction equation

HRID 980235 reaction equation
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:20][C:21]1[C:29]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](O)=[O:24]>C(Cl)Cl.CN1CCOCC1.ClC(OCC(C)C)=O>[C:11]1([CH2:10][C@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[C:17]2[O:19][C:23](=[O:24])[C:22]3[CH:26]=[CH:27][CH:28]=[C:29]([C:30]([F:31])([F:32])[F:33])[C:21]=3[N:20]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 6045692-Amino-3-(trifluoromethyl)benzoic acid

Product 1

HCID 13578785HCID 13578785, compoundYield 44.5%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent3×HCID 79724-MethylmorpholineSolvent2×HCID 62365Isobutyl chloroformateSolvent

Procedure

Using the procedure of Step A of Example 7, a solution of 19.9 g of BOC-L-phenylalanine in 150 ml of methylene chloride and 20.6 ml of N-methyl-morpholine, 19.5 ml of isobutyl chloroformate in 75 ml of methylene chloride and 15.4 g of 2-amino-3-trifluoromethyl benzoic acid in 150 ml of methylene chloride and 8.3 ml of N-methyl-morpholine were reacted to obtain 14.5 g of 1,1-dimethylethyl N-[(S) 2-phenyl-1-[4-oxo-8-(trifluoromethyl)-4H-3,1-benzoxazin-2-yl]-ethyl]-carbamate melting at 145° C. and having a specific rotation of [α]D =-33.5°±2° (c=0.5% in CH3COOH).

Sources & evidence

ORD record
ord-79dff35baf8b4571af8b261c36e3caae
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

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