(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid → {(S)-1-[(S)-1-(2-Methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester

HRID 1481903Notes

Reaction equation

HRID 1481903 reaction equation
[C:1]([O:5][C:6](=[O:40])[N:7]([C@H:9]([C:11](=[O:39])[NH:12][C@@H:13]1[C:19](=[O:20])[N:18]([CH2:21][C:22]2[C:31]3[C:26](=[C:27](Br)[CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][C:23]=2[O:33][CH3:34])[C:17]2[CH:35]=[CH:36][CH:37]=[CH:38][C:16]=2[NH:15][CH2:14]1)[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.N[C@@H]1C(=O)N(CC2C3C(=CC=CC=3)C=CC=2OC)C2C=CC=CC=2NC1.N(C(OC(C)(C)C)=O)(C)[C@H](C(O)=O)C>>[C:1]([O:5][C:6](=[O:40])[N:7]([C@H:9]([C:11](=[O:39])[NH:12][C@@H:13]1[C:19](=[O:20])[N:18]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][C:23]=2[O:33][CH3:34])[C:17]2[CH:35]=[CH:36][CH:37]=[CH:38][C:16]=2[NH:15][CH2:14]1)[CH3:10])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 90220831{(S)-1-[(S)-1-(5-Bromo-2-methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester2×HCID 90221037(S)-3-amino-1-(2-methoxy-naphthalen-1-ylmethyl)-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one trifluoroacetate salt

Product 1

HCID 90220896{(S)-1-[(S)-1-(2-Methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl esterYield 73.2%

Procedure

In a similar manner to that described for the preparation of {(S)-1-[(S)-1-(5-bromo-2-methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (Intermediate 12), (S)-3-amino-1-(2-methoxy-naphthalen-1-ylmethyl)-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one trifluoroacetate salt (Step 1 above) (460 mg) and Boc-N-Me-Ala-OH (223.3 mg, 1.1 mmol) were converted to the title compound (390 mg, 73.2%) obtained as a white solid. LC-MS: 533 (M+H).

Sources & evidence

ORD record
ord-258b5d92561c467f88f9dd29235aa73d
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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