Ethyl Acetate → Benzyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-(3-hydroxyadamantan-1-yl)-2-oxo ethyl]carbamate

HRID 1184041

Reaction equation

HRID 1184041 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:16]12[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][C:18](O)([CH2:19]3)[CH2:17]1)[CH2:23]2)[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=N1.C(N(CC)C(C)C)(C)C.C(OCC)(=[O:48])C>C(#N)C>[C:32]([C@@H:33]1[CH2:34][C@H:35]2[C@H:31]([CH2:36]2)[N:30]1[C:13](=[O:15])[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:16]12[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][C:18]([OH:48])([CH2:19]3)[CH2:17]1)[CH2:23]2)#[N:28]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86703400(2S)-2-{[(benzyloxy)carbonyl]amino}-2-(3-hydroxyadamantan-1-yl)acetic acid

Product 1

HCID 86703399Benzyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-(3-hydroxyadamantan-1-yl)-2-oxo ethyl]carbamateYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

(2S)-2-{[(Benzyloxy)carbonyl]amino}-2-(3-hydroxyadamantan-1-yl)acetic acid of formula-XIV (20 gm), (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile PTSA salt of Formula-XIII (16 gm), 1-ethyl-3-(3-dimethylaminoporpyl)carbodiimide (12 gm) and 1-hydroxy benzotriazole (1.2 gm) were dissolved in ethyl acetate (20 ml) and acetonitrile (40 ml). The reaction mixture was cooled to 20° C. Then addition of N,N-diisopropylethylamine (16 gm) was carried out for 15 min. The reaction mixture was stirred for 8 hrs and washed with 2N HCl solution. Organic phase was washed with NaHCO3 solution, dried and evaporated to yield 19.8 gm (80%) of title product. MP: 105-106° C.

Workup

  1. washwashed with 2N HCl solution
  2. washOrganic phase was washed with NaHCO3 solution
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-7ebb6d6745c240d29936509fce7993da
Source dataset
uspto-grants-2014_03
Patent number
US08664443B2

Linked notes

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