Methylamine → 2(R)-Benzyl-9-benzyloxy-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7,7-dimethylnonanoic acid (N-methyl)amide

HRID 863323Notes

Reaction equation

HRID 863323 reaction equation
[CH3:1][NH2:2].[CH2:3]([C@@H:10]1[CH2:14][C@@H:13]([C@@H:15]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:16][C:17]([CH3:29])([CH3:28])[CH2:18][CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:12][C:11]1=[O:38])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(NC(=O)[C@H](C(C)C)C[C@H](O)[C@@H](NC(OC(C)(C)C)=O)CC(C)(C)CC(N1C2C=CC=CC=2SC(C(NCC)=O)C1)=O)CCC>O1CCCC1>[CH3:1][NH:2][C:11](=[O:38])[C@H:10]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:14][C@H:13]([OH:12])[C@@H:15]([NH:30][C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[CH2:16][C:17]([CH3:29])([CH3:28])[CH2:18][CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 676254563(R)-Benzyl-5(S)-[5-benzyloxy-1(S)-tert-butoxycarbonylamino-3,3-dimethyl-pentyl]-2-oxotetrahydrofuranHCID 1317205345(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(S)-isopropyl-7,7dimethyl-8-[2(R,S)-ethylaminocarbonyl-3,4-dihydro-2H1,4-benzothiazin-4-ylcarbonyl]-octanoic acid (N-butyl)amide

Product 1

HCID 541739802(R)-Benzyl-9-benzyloxy-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7,7-dimethylnonanoic acid (N-methyl)amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8 ml of methylamine are passed into a solution of 476 mg of 3(R)-benzyl-5(S)-[5-benzyloxy-1(S)-tert-butoxycarbonylamino-3,3-dimethyl-pentyl]-2-oxotetrahydrofuran (Example 74d)) in 4 ml of tetrahydrofuran at 0° C. and a condensation reaction is carried out. The solution is stirred at room temperature for 30 h and concentrated and the residue is further reacted without chromatography: Rf (L)=0.48; FAB-MS:(M+H)+ =527.

Workup

  1. customat 0° C.
  2. customa condensation reaction
  3. concentrationconcentrated
  4. customthe residue is further reacted without chromatography

Sources & evidence

ORD record
ord-ad0da3c15f464710babd0e425df9caec
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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