Tert-Butylamine → Boc-Hyp-NH-tBu

HRID 427384Notes

Reaction equation

HRID 427384 reaction equation
[C:1]([N:8]1[CH2:16][C@H:14]([OH:15])[CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:17]([NH2:21])([CH3:20])([CH3:19])[CH3:18].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>ClCCl>[N:8]1([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:16][C@H:14]([OH:15])[CH2:13][C@H:9]1[C:10]([NH:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:12]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 757711-HydroxybenzotriazoleHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 10334194Boc-Hyp-NH-tBuYield 189%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a dichloromethane solution containing 5.1 g of N-Boc-hydroxyproline (Boc-Hyp-OH), 0.35 g of tert-butylamine, 7.4 g of HOBt and 6.0 g of EDC hydrochloride were added under ice cooling and the resultant mixture was stirred overnight at room temperature. The reaction mixture was treated similarly to that in Example 144 (Process 2) to give 2.59 g of the title compound.

Workup

  1. additionwere added under ice cooling
  2. additionThe reaction mixture was treated similarly to that in Example 144 (Process 2)

Sources & evidence

ORD record
ord-1b10a96c5e5d43d99a4e3cf4b8a38248
Source dataset
uspto-grants-2001_11
Patent number
US06313094B1

Reaction notes

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